U.S. patent application number 10/570013 was filed with the patent office on 2007-02-01 for insecticide for agricultural or horticultural use and method of use thereof.
This patent application is currently assigned to MITSUI CHEMICALS., INC.. Invention is credited to Shinichi Banba, Yutaka Chiba, Hidenori Daido, Akiyoshi Kai, Hiroko Kato, Hiroyuki Katsuta, Atsuko Kawahara, Nobuyuki Kawahara, Junji Maki, Michikazu Nomura, Kiyoshi Takahashi, Takeo Wakita, Kei Yoshida.
Application Number | 20070027154 10/570013 |
Document ID | / |
Family ID | 34269364 |
Filed Date | 2007-02-01 |
United States Patent
Application |
20070027154 |
Kind Code |
A1 |
Yoshida; Kei ; et
al. |
February 1, 2007 |
Insecticide for agricultural or horticultural use and method of use
thereof
Abstract
An object of the present invention is to provide insecticides
having high effectiveness. The present invention provides compounds
represented by formula (1): ##STR1## wherein A.sub.1, A.sub.2,
A.sub.3, and A.sub.4 independently represent a carbon atom, a
nitrogen atom, or an oxidized nitrogen atom; R.sub.1 represents a
C1-C6 alkyl group which may be substituted, a phenyl group which
may be substituted, or a heterocyclic group which may be
substituted; R.sub.2 and R.sub.3 independently represent a hydrogen
atom, a C1-C4 alkyl group which may be substituted, or a C1-C4
alkylcarbonyl group which may be substituted; G.sub.1, G.sub.2, and
G.sub.3 independently represent an oxygen atom or a sulfur atom; Xs
may be the same or different and each represent a hydrogen atom, a
halogen atom, a C1-C4 alkyl group which may be substituted, or an
amino group which may be substituted; n represents an integer of 0
to 4; Q represents a phenyl group which may be substituted, a
naphthyl group which may be substituted, a tetrahydronaphthyl group
which may be substituted, or a heterocyclic group which may be
substituted, insecticides containing the compounds as active
ingredients, and a method for producing the compounds. The
compounds represented by formula (1) exhibit an excellent
preventive effect as insecticides and also exhibit an excellent
preventive effect when being combined with another insecticide, an
acaricide, a nematocide, a fungicide, a herbicide, a plant growth
regulator, or a biological pesticide.
Inventors: |
Yoshida; Kei; (Mobara-shi,
JP) ; Wakita; Takeo; (Mobara-shi, JP) ;
Katsuta; Hiroyuki; (Mobara-shi, JP) ; Kai;
Akiyoshi; (Mobara-shi, JP) ; Chiba; Yutaka;
(Mobara-shi, JP) ; Takahashi; Kiyoshi;
(Mobara-shi, JP) ; Kato; Hiroko; (Mobara-shi,
JP) ; Kawahara; Nobuyuki; (Mobara-shi, JP) ;
Nomura; Michikazu; (Mobara-shi, JP) ; Daido;
Hidenori; (Mobara-shi, JP) ; Maki; Junji;
(Mobara-shi, JP) ; Banba; Shinichi; (Mobara-shi,
JP) ; Kawahara; Atsuko; (Mobara-shi, JP) |
Correspondence
Address: |
BUCHANAN, INGERSOLL & ROONEY PC
POST OFFICE BOX 1404
ALEXANDRIA
VA
22313-1404
US
|
Assignee: |
MITSUI CHEMICALS., INC.
Tokyo
JP
|
Family ID: |
34269364 |
Appl. No.: |
10/570013 |
Filed: |
August 23, 2004 |
PCT Filed: |
August 23, 2004 |
PCT NO: |
PCT/JP04/12416 |
371 Date: |
February 28, 2006 |
Current U.S.
Class: |
514/241 ;
514/242; 514/252.05; 514/255.05; 514/256; 514/341; 544/183;
544/209; 544/238; 544/331; 544/405; 546/272.7; 546/275.1 |
Current CPC
Class: |
C07C 2601/04 20170501;
C07C 323/42 20130101; A01N 47/20 20130101; C07C 237/40 20130101;
C07C 211/48 20130101; C07C 317/36 20130101; C07C 317/18 20130101;
C07C 215/68 20130101; C07C 2601/08 20170501; C07C 271/28 20130101;
C07C 323/12 20130101; C07C 333/08 20130101; C07C 327/48 20130101;
C07C 323/36 20130101; C07C 317/40 20130101; C07C 265/12 20130101;
C07D 213/81 20130101; C07C 211/47 20130101 |
Class at
Publication: |
514/241 ;
514/242; 514/252.05; 514/255.05; 514/256; 514/341; 544/183;
544/209; 544/238; 544/331; 544/405; 546/275.1; 546/272.7 |
International
Class: |
A61K 31/53 20070101
A61K031/53; A61K 31/506 20070101 A61K031/506; A61K 31/501 20070101
A61K031/501; A61K 31/497 20070101 A61K031/497; A61K 31/4439
20070101 A61K031/4439; C07D 403/02 20070101 C07D403/02 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 29, 2003 |
JP |
2003-305816 |
Claims
1. A compound represented by formula (1): ##STR33## wherein
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.1
represents a C1-C6 alkyl group which may be substituted, a phenyl
group which may be substituted, a naphthyl group which may be
substituted, or a heterocyclic group which may be substituted;
R.sub.2 and R.sub.3 independently represent a hydrogen atom, a
C1-C4 alkyl group which may be substituted, or a C1-C4
alkylcarbonyl group which may be substituted; G.sub.1, G.sub.2, and
G.sub.3 independently represent an oxygen atom or a sulfur atom; Xs
may be the same or different and each represent a hydrogen atom, a
halogen atom, a C1-C4 alkyl group which may be substituted, or an
amino group which may be substituted; n represents an integer of 0
to 4; Q represents a phenyl group which may be substituted, a
naphthyl group which may be substituted, a tetrahydronaphthyl group
which may be substituted, or a heterocyclic group which may be
substituted.
2. The compound according to claim 1, wherein in formula (1),
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.1
represents: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6
alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a
C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a phenyl group, a substituted phenyl group
having one or more substituents which may be the same or different
and which are selected from a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl
group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl
group, a naphthyl group, a substituted naphthyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), a substituted heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a
thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,
-E.sub.1-Z.sub.1-R.sub.4 (wherein E.sub.1 represents a C1-C4
alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group,
a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a
C3-C4 haloalkynylene group; R.sub.4 represents a hydrogen atom, a
C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a
C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6
haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a phenyl group, a substituted phenyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
naphthyl group, a substituted naphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), or a substituted heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a
thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group); and
Z.sub.1 represents --O--, --S--, --SO--, --SO.sub.2--,
--C(.dbd.O)--, --C(.dbd.O)O--, --OC(.dbd.O)--, --N(R.sub.5)--,
--C(.dbd.O)N(R.sub.5)--, or --N(R.sub.5)C(.dbd.O)-- (R.sub.5
represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, or a C1-C4
alkoxycarbonyl group)), or -E.sub.2-R.sub.6 (wherein E.sub.2
represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a
C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4
haloalkenylene group, or a C3-C4 haloalkynylene group, and R.sub.6
represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,
a cyano group, a nitro group, a hydroxyl group, a phenyl group, a
substituted phenyl group having one or more substituents which may
be the same or different and which are selected from a halogen
atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted
naphthyl group having one or more substituents which may be the
same or different and which are selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, a
pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4
haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a
C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents
a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a
pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl
group, a tetrahydrothienyl group, a tetrahydropyranyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a
pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl
group, or a tetrazolyl group), or a substituted heterocyclic group
(which represents a pyridyl group, a pyridine-N-oxide group, a
pyrimidinyl group, a pyridazyl group, a furyl group, a
tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group,
a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group,
an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a
thiadiazolyl group, a pyrrole group, an imidazolyl group, a
triazolyl group, a pyrazolyl group, or a tetrazolyl group) having
one or more substituents which may be the same or different and
which are selected from a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl
group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl
group); R.sub.2 and R.sub.3 independently represent a hydrogen
atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4
haloalkylcarbonyl group; G.sub.1, G.sub.2, and G.sub.3
independently represent an oxygen atom or a sulfur atom; Xs may be
the same or different and each represent a hydrogen atom, a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy
group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4
haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4
haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4
haloalkylsulfonyl group, a cyano group, a nitro group, an amino
group, or an amino group which may be substituted by a C1-C4 alkyl
group; n represents an integer of 0 to 4; and Q represents a phenyl
group, a substituted phenyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a
C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a phenyl group, a substituted phenyl group (which may have
the same or different substituents selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group,
a hydroxyl group, and a pentafluorosulfanyl group), a thienyl
group, and a substituted thienyl group (which may have the same or
different substituents selected from a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
haloalkylsulfonyloxy group, a cyano group, a nitro group, a
hydroxyl group, and a pentafluorosulfanyl group), a naphthyl group,
a substituted naphthyl group having one or more substituents which
may be the same or different and which are selected from a halogen
atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
halo alkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, and a pentafluorosulfanyl group, a heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a thienyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a
pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl
group, or a tetrazolyl group), a substituted heterocyclic group
(which represents a pyridyl group, a pyridine-N-oxide group, a
pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group, a tetrahydronaphthyl group, or a
substituted tetrahydronaphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group (excluding case (1) in which Q represents
a 3,4-dichlorophenyl group when R1 represents a methyl group, case
(2) in which Q represents an unsubstituted phenyl group when R1
represents an ethyl group, and case (3) in which Q represents an
unsubstituted pyridyl group when R1 represents an unsubstituted
phenyl group.)
3. The compound according to claim 2, wherein in formula (1),
G.sub.1 and G.sub.3 each represent an oxygen atom, and Q represents
a phenyl group, a substituted phenyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 haloalkylsulfonyloxy group, a C1-C4 alkylcarbonyl
group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro
group, a hydroxyl group, and a pentafluorosulfanyl group, a
naphthyl group, a substituted naphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group, a heterocyclic group (which represents a
pyridyl group or a pyrazolyl group), a substituted heterocyclic
group (which represents a pyridyl group or a pyrazolyl group)
having one or more substituents which may be the same or different
and which are selected from a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 haloalkyl group which may be substituted by at least
one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group, a tetrahydronaphthyl group, or a
substituted tetrahydronaphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group.
4. The compound according to claim 3, wherein in formula (1), Xs
may be the same or different and each represent a hydrogen atom, a
halogen atom, a C1-C4 alkyl group, or a trifluoromethyl group, and
n is an integer of 0 to 4.
5. The compound according to claim 4, wherein in formula (1),
R.sub.1 represents: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a
C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl
group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, -E.sub.1-Z.sub.1-R.sub.4 (wherein E.sub.1
represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a
C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4
haloalkenylene group, or a C3-C4 haloalkynylene group, R.sub.4
represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl
group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6
haloalkenyl group, a C2-C6 haloalkynyl group, and Z, represents
--O--, --S--, --SO--, or --SO.sub.2--), or -E.sub.2-R.sub.6
(wherein E.sub.2 represents a C1-C4 alkylene group, a C2-C4
alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene
group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene
group, and R.sub.6 represents a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a cyano group, a nitro group, a hydroxyl
group, a phenyl group, a substituted phenyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6
alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl
group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy
group, a C1-C4 alkoxycarbonyl group, and a pentafluorosulfanyl
group, a pyridyl group, a substituted pyridyl group having one or
more substituents selected from a halogen atom, a C1-C6 haloalkyl
group, and a C1-C6 haloalkoxy group, a thienyl group, or a
tetrahydrofuryl group).
6. The compound according to claim 5, wherein in formula (1),
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 are all carbon atoms, or one
any of A.sub.1, A.sub.2, A.sub.3, and A.sub.4 is a nitrogen atom or
an oxidized nitrogen atom, and G.sub.2 is an oxygen atom.
7. The compound according to claim 6, wherein in formula (1), Q
represents a phenyl group, a substituted phenyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a pentafluorosulfanyl group, a cyano group, and a nitro
group; a pyridyl group, or a substituted pyridyl group having one
or more substituents which may be the same or different and which
are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a pentafluorosulfanyl group, a cyano group, and a nitro
group.
8. The compound according to claim 7, wherein in formula (1), Q is
a substituent represented by formula (1-2) or (1-3): ##STR34##
(wherein Y.sub.1, Y.sub.2, Y.sub.4, and Y.sub.5 may be the same or
different and each represent a hydrogen atom, a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a
C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano
group, or a nitro group, and Y.sub.3 represents a C1-C6 haloalkyl
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6
haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6
haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only
one of Y.sub.1 and Y.sub.5 represents a hydrogen atom) ##STR35##
(wherein Y.sub.6, Y.sub.7, and Y.sub.9 may be the same or different
and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a pentafluorosulfanyl group, a cyano group, or a nitro
group, and Y.sub.8 represents a C1-C6 haloalkyl group, a C1-C6
haloalkoxy group, a C1-C6 haloalkyl group which may be substituted
by at least one hydroxyl group, a C1-C6 haloalkylthio group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or
a pentafluorosulfanyl group, but only one of Y.sub.6 and Y.sub.9
represents a hydrogen atom).
9. A compound represented by formula (2): ##STR36## wherein
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom, and
R.sub.1 represents the following: a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a phenyl group, a
substituted phenyl group having one or more substituents which may
be the same or different and which are selected from a halogen
atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted
naphthyl group having one or more substituents which may be the
same or different and which are selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 halo alkyl sulfonyl
group, a cyano group, a nitro group, a hydroxyl group, a
pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4
haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a
C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents
a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a
pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl
group, a tetrahydrothienyl group, a tetrahydropyranyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a
pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl
group, or a tetrazolyl group), a substituted heterocyclic group
(which represents a pyridyl group, a pyridine-N-oxide group, a
pyrimidinyl group, a pyridazyl group, a furyl group, a
tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group,
a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group,
an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a
thiadiazolyl group, a pyrrole group, an imidazolyl group, a
triazolyl group, a pyrazolyl group, or a tetrazolyl group) having
one or more substituents which may be the same or different and
which are selected from a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl
group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl
group), or -E.sub.1-Z.sub.1-R.sub.4 (wherein E.sub.1 represents a
C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene
group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or
a C3-C4 haloalkynylene group; R.sub.4 represents a hydrogen atom, a
C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a
C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6
haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a phenyl group, a substituted phenyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
naphthyl group, a substituted naphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), a substituted heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a
thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group), and
Z.sub.1 represents --O--, --S--, --SO--, --SO.sub.2--,
--C(.dbd.O)--, --C(.dbd.O)O--, --OC(.dbd.O)--, --N(R.sub.5)--,
--C(.dbd.O)N(R.sub.5)--, or --N(R.sub.5)C(.dbd.O)-- (R.sub.5
represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4
alkylcarbonyl group, or a C1-C4 alkoxycarbonyl group)), or
-E.sub.2-R.sub.6 (wherein E.sub.2 represents a C1-C4 alkylene
group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4
haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4
haloalkynylene group, and R.sub.6 represents a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group,
a hydroxyl group, a phenyl group, a substituted phenyl group having
one or more substituents which may be the same or different and
which are selected from a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl
group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl
group, a naphthyl group, a substituted naphthyl group having one or
more substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a
heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), or a substituted heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a
thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl
group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro
group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4
alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group); R.sub.2
represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4
alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G.sub.1,
G.sub.2, and G.sub.3 independently represents an oxygen atom or a
sulfur atom; Xs may be the same or different and each represent a
hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4
haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a
C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4
alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4
alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano
group, a nitro group, or an amino group which may be substituted by
a C1-C4 alkyl group; n represents an integer of 0 to 4; and Hal
represents a halogen atom (excluding a case in which R1 is an
unsubstituted benzyl group when X is a hydrogen atom.}
10. A compound represented by formula (3): ##STR37## wherein
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.3
represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4
alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G.sub.3
represents an oxygen atom or a sulfur atom; Xs may be the same or
different and each represent a hydrogen atom, a halogen atom, a
C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a
C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4
haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4
haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4
haloalkylsulfonyl group, a cyano group, a nitro group, or an amino
group which may be substituted by a C1-C4 alkyl group; n represents
an integer of 0 to 4; and Q represents a phenyl group, a
substituted phenyl group having one or more substituents which may
be the same or different and which are selected from a halogen
atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a
C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a phenyl group, a substituted phenyl group (which may have
the same or different substituents selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro
group, a hydroxyl group, and a pentafluorosulfanyl group), a
thienyl group, a substituted thienyl group (which may have the same
or different substituents selected from a halogen atom, a C1-C6
alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a
C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro
group, a hydroxyl group, and a pentafluorosulfanyl group), a
naphthyl group, a substituted naphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl
group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6
haloalkyl group which may be substituted by at least one hydroxyl
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano
group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl
group, a heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a thienyl group, an oxazolyl group, an isoxazolyl
group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl
group, a thiadiazolyl group, a pyrrole group, an imidazolyl group,
a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a
substituted heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a thienyl group, an oxazolyl group, an isoxazolyl
group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl
group, a thiadiazolyl group, an imidazolyl group, a triazolyl
group, a pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group, a tetrahydronaphthyl group, or a
substituted tetrahydronaphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group.
11. A compound represented by formula (4): ##STR38## wherein
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.2
and R.sub.3 independently represent a hydrogen atom, a C1-C4 alkyl
group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl
group; G.sub.3 represents an oxygen atom or a sulfur atom; Xs may
be the same or different and each represent a hydrogen atom, a
halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4
alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a
C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4
haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4
haloalkylsulfonyl group, a cyano group, a nitro group, or an amino
group which may be substituted by a C1-C4 alkyl group; n represents
an integer of 0 to 4; and Q is a substituent represented by formula
(1-2) or (1-3): ##STR39## (wherein Y.sub.1, Y.sub.2, Y.sub.4, and
Y.sub.5 may be the same or different and each represent a hydrogen
atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group,
a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano
group, or a nitro group, and Y.sub.3 represents a C1-C6 haloalkyl
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6
haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6
haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only
one of Y.sub.1 and Y.sub.5 represents a hydrogen atom); ##STR40##
(wherein Y.sub.6, Y.sub.7, and Y.sub.9 may be the same or different
and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C I--C6 haloalkylsulfonyl
group, a pentafluorosulfanyl group, a cyano group, or a nitro
group, and Y.sub.8 represents a C I--C6 haloalkyl group, a C I--C6
haloalkoxy group, a C1-C6 haloalkyl group which may be substituted
by at least one hydroxyl group, a C1-C6 haloalkylthio group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or
a pentafluorosulfanyl group, but only one of Y.sub.6 and Y.sub.9
represents a hydrogen atom).
12. A method for producing the compound according to claim 1, the
method comprising reacting the compound represented by formula (2)
according to claim 9 with a compound represented by formula (5):
##STR41## wherein R.sub.3 and Q each represent the same as in claim
1.
13. A method for producing the compound according to claim 1, the
method comprising reacting the compound represented by formula (3)
according to claim 10 with a compound represented by formula (6):
H-G.sub.2-R.sub.1 (6) wherein R.sub.1 and G.sub.2 each represent
the same as in claim 1.
14. A method for producing the compound according to claim 1, the
method comprising reacting the compound represented by formula (4)
according to claim 11 with a compound represented by formula (7):
##STR42## wherein R.sub.1, G.sub.1, and G.sub.2 each represent the
same as in claim 1.
15. An aniline derivative represented by formula (8): ##STR43##
wherein R.sub.7 represents a C1-C6 haloalkyl group, Y.sub.10,
Y.sub.11, Y.sub.12, and Y.sub.13 may be the same or different and
each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a pentafluorosulfanyl group, a cyano group, or a nitro
group, and R.sub.8 and R.sub.9 independently represent a hydrogen
atom, a C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted
m-nitrobenzoyl group, and m represents 0, 1, or 2.
16. An aniline derivative represented by formula (9): ##STR44##
wherein R.sub.10 represents a C1-C6 haloalkyl group which may be
substituted by at least one hydroxyl group, Y.sub.14, Y.sub.15,
Y.sub.16, and Y.sub.17 may be the same or different and each
represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a
C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a
pentafluorosulfanyl group, a cyano group, or a nitro group, and
R.sub.11 and R.sub.12 independently represent a hydrogen atom, a
C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted
m-nitrobenzoyl group.
17. An insecticide comprising the compound according to claim 1 as
an active ingredient.
18. An agricultural/horticultural insecticide comprising the
compound according to claim 1 as an active ingredient.
19. A method for using a chemical comprising treating a useful crop
or soil with an effective amount of the compound according to claim
1, for protecting the useful crop from harmful organisms.
20. A method for preventing pests comprising using the compound
according to claim 1 and at least one fungicide and/or insecticide
in combination.
21. The method for preventing pests according to claim 20, wherein
the fungicide and/or insecticide is selected from azole fungicides
such as triadimefon, hexaconazole, propiconazole, ipconazole,
prochloraz, and triflumizole; pyrimidine fungicides such as
pyrifenox and fenarimol; anilinopyrimidine fungicides such as
mepanipyrim and cyprodinil; acylalanine fungicides such as
metalaxyl, oxadixyl, and benalaxyl; benzimidazole fungicides such
as thiophanate-methyl and benomyl; dithiocarbamate fungicids such
as mancozeb, propineb, zineb, and metiram; organochlorine
fungicides such as tetrachloroisophthalonitrile; carboxamide
fungicides such as carpropamid and ethaboxam; morpholine fungicides
such as dimethomorph; strobilurin fungicides such as azoxystrobin,
kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin,
trifloxystrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin;
dicarboxyimide fungicides such as iprodione and procymidone;
soil-applied fungicides such as flusulfamide, dazomet, methyl
isothiocyanate, and chloropicrin; copper fungicides such as basic
copper chloride, basic copper sulfate, copper nonylphenol
sulfonate, oxine-copper, and DBEDC; inorganic fungicides such as
sulfur and zinc sulfate; organophosphate fungicides such as
edifenphos, tolclofos-methyl, and fosetyl-aluminum; melanin
biosynthesis inhibitors such as phthalide, tricyclazole,
pyroquilon, and diclocymet; antibiotics such as kasugamycin,
validamycin, and polyoxins; fungicidal natural products such as
repe seed oil; and other fungicides such as
benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid,
quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid,
proquinazid, silthiofam, oxypoconazole, famoxadone, cyazofamid,
fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole,
chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet,
dichlofluanid,
(RS)--N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoromethyl-1-
H-pyrazole-4-carboxamide(penthiopyrad; ISO proposed), oxycarboxin,
mepronil, flutolanil, triforine, oxolinic acid, probenazole,
acibenzolar-S-methyl, isoprothiolane, ferimzone, diclomezine,
pencycuron, fluoroimide, chinomethionate, iminoctadine-triacetate,
and iminoctadine-albesilate; synthetic pyrethroid insecticides such
as allethrin, tetramethrin, resmethrin, phenothrin, furamethrin,
permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin,
fenpropathrin, tralomethrin, cycloprothrin, flucythrinate,
fluvalinate, acrinathrin, tefluthrin, bifenthrin, empenthrin,
beta-cyfluthrin, zeta-cypermethrin, and fenvalerate, and various
isomers thereof and pyrethrum extracts; organophosphate
insecticides such as DDVP, cyanophos, fenthion, fenitrothion,
tetrachlorvinphos, dimethylvinphos, propaphos, methylparathion,
temephos, phoxim, acephate, isofenphos, salithion, DEP, EPN,
ethion, mecarbam, pyridafenthion, diazinon, pirimiphos-methyl,
etrimfos, isoxathion, quinalphos, chlorpyrifos-methyl,
chlorpyrifos, phosalone, phosmet, methidathion, oxydeprofos,
vamidothion, malathion, phenthoate, dimethoate, formothion,
thiometon, ethylthiometon, phorate, terbufos, profenofos,
prothiofos, sulprofos, pyraclofos, monocrotophos, naled,
fosthiazate, and cadusafos; carbamate insecticides such as NAC,
MTMC, MIPC, BPMC, XMC, PHC, MPMC, ethiofencarb, bendiocarb,
pirimicarb, carbosulfan, benfuracarb, methomyl, oxamyl, and
aldicarb; arylpropylether insecticides such as etofenprox and
halfenprox; silylether insecticides such as silafluofen;
insecticidal natural products such as nicotine-sulfate, polynactin
complex, abamectin, milbemectin, and BT agents; insecticides such
as, cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron,
teflubenzuron, triflumuron, flufenoxuron, flucycloxuron,
hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid,
dinotefuran, pymetrozine, fipronil, buprofezin, fenoxycarb,
pyriproxyfen, methoprene, hydroprene, kinoprene, diafenthiuron,
triazamate, tebufenozide, and endosulfan; acaricides such as
dicofol, chlorobenzilate, bromopropylate, tetradifon, CPCBS, BPPS,
chinomethionate, amitraz, benzoximate, hexythiazox, fenbutatin
oxide, cyhexatin, dienochlor, clofentezine, pyridaben,
fenpyroximate, fenazaquin, and tebufenpyrad; novaluron;
noviflumuron; emamectin benzoate; clothianidin; thiacloprid;
thiamethoxam; flupyrazofos; acequinocyl; bifenazate;
chromafenozide; etoxazole; fluacrypyrim; flufenzine; halofenozide;
indoxacarb; methoxyfenozide; spirodiclofen; tolfenpyrad;
gamma-cyhalothrin; ethiprole; amidoflumet; bistrifluron;
flonicamid; flubrocythrinate; flufenerim; pyridalyl; pyrimidifen;
spinosad; and spiromesifen.
Description
TECHNICAL FIELD
[0001] The present invention relates to compounds represented by
formula (1), insecticides containing the compounds as active
ingredients, a method for producing the insecticides, and a method
for using the insecticides.
BACKGROUND ART
[0002] PCT Japanese Translation Patent Publication No. 11-511442
discloses salicylic compounds similar to compounds of the present
invention. However, compounds represented by formula (1) of the
present invention do not have a salicylic skeleton, and the
compounds disclosed in the above publication are clearly outside
the scope of claims of the present invention.
[0003] Publication No. WO2003-22806 discloses compounds as
production intermediates similar to the compounds of the present
invention, but it does not disclose an activity to insects. Also,
the compounds disclosed in the publication are clearly outside the
scope of claims of the present invention.
[0004] J. Org. Chem. 142 (1966) discloses compounds as production
intermediates similar to the compounds of the present invention,
but it does not disclose an activity to insects. Also, the
compounds disclosed in the publication are clearly outside the
scope of claims of the present invention.
[0005] J. Am. Chem. Soc. 6382 (2000) discloses compounds as
production intermediates similar to the compounds of the present
invention, but it does not disclose an activity to insects. Also,
the compounds disclosed in the publication are clearly outside the
scope of claims of the present invention.
DISCLOSURE OF INVENTION
[0006] An object of the present invention is to provide
insecticides having high effectiveness.
[0007] As a result of intensive research for achieving the object,
the inventors found that the compounds of the present invention are
novel compounds not disclosed in any document and have an excellent
insecticidal effect, and the compounds can be used as new
insecticides. It is also found that intermediates in production of
the compounds of the present invention are not disclosed in any
document and are useful production intermediates. The present
invention has been achieved based on these findings.
[0008] The present invention provides compounds represented by the
following formulae:
[0009] [1] Compounds represented by formula (1) ##STR2## wherein
A.sub.1, A.sub.2, A.sub.3, and A.sub.4 independently represent a
carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.1
represents a C1-C6 alkyl group which may be substituted, a phenyl
group which may be substituted, or a heterocyclic group which may
be substituted; R.sub.2 and R.sub.3 independently represent a
hydrogen atom, a C1-C4 alkyl group which may be substituted, or a
C1-C4 alkylcarbonyl group which may be substituted; G.sub.1,
G.sub.2, and G.sub.3 independently represent an oxygen atom or a
sulfur atom; Xs may be the same or different and each represent a
hydrogen atom, a halogen atom, a C1-C4 alkyl group which may be
substituted, or an amino group which may be substituted; n
represents an integer of 0 to 4; Q represents a phenyl group which
may be substituted, a naphthyl group which may be substituted, a
tetrahydronaphthyl group which may be substituted, or a
heterocyclic group which may be substituted.
[0010] [2] Compounds represented by formula (1) wherein A.sub.1,
A.sub.2, A.sub.3, and A.sub.4 independently represent a carbon
atom, a nitrogen atom, or an oxidized nitrogen atom; R.sub.1
represents the following:
a C1-C6 alkyl group,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group,
a C2-C6 haloalkynyl group,
a C3-C6 cycloalkyl group,
a C3-C6 halocycloalkyl group,
a phenyl group,
[0011] a substituted phenyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
a naphthyl group,
[0012] a substituted naphthyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
[0013] a heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group),
[0014] a substituted heterocyclic group (which represents a pyridyl
group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl
group, a furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group) having one or more substituents which may be
the same or different and which are selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, a
pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4
haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a
C1-C4 alkoxycarbonyl group,
-E.sub.1-Z.sub.1-R.sub.4
[0015] (wherein E.sub.1 represents a C1-C4 alkylene group, a C2-C4
alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene
group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene
group; R.sub.4 represents a hydrogen atom, a C1-C6 alkyl group, a
C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl
group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group,
a C3-C8 cycloalkyl group,
a C3-C8 halocycloalkyl group,
a phenyl group,
[0016] a substituted phenyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
a naphthyl group,
[0017] a substituted naphthyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
[0018] a heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), or
[0019] a substituted heterocyclic group (which represents a pyridyl
group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl
group, a furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group) having one or more substituents which may be
the same or different and which are selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, a
pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4
haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a
C1-C4 alkoxycarbonyl group), and
[0020] Z.sub.1 represents --O--, --S--, --SO--, --SO.sub.2--,
--C(.dbd.O)--, --C(.dbd.O)O--, --OC(.dbd.O)--, --N(R.sub.5)--,
--C(.dbd.O)N(R.sub.5)--, or --N(R.sub.5)C(.dbd.O)-- (R.sub.5
represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4
alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, or a C1-C4
alkoxycarbonyl group)), or -E.sub.2-R.sub.6
[0021] (wherein E.sub.2 represents a C1-C4 alkylene group, a C2-C4
alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene
group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene
group, and R.sub.6 represents a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group,
a cyano group,
a nitro group,
a hydroxyl group,
a phenyl group,
[0022] a substituted phenyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
a naphthyl group,
[0023] a substituted naphthyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a
C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and
a C1-C4 alkoxycarbonyl group,
[0024] a heterocyclic group (which represents a pyridyl group, a
pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a
furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group), or
[0025] a substituted heterocyclic group (which represents a pyridyl
group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl
group, a furyl group, a tetrahydrofuryl group, a thienyl group, a
tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl
group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl
group, an isothiazolyl group, a thiadiazolyl group, a pyrrole
group, an imidazolyl group, a triazolyl group, a pyrazolyl group,
or a tetrazolyl group) having one or more substituents which may be
the same or different and which are selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, a
pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4
haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a
C1-C4 alkoxycarbonyl group);
[0026] R.sub.2 and R.sub.3 independently represent a hydrogen atom,
a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4
haloalkylcarbonyl group; G.sub.1, G.sub.2, and G.sub.3
independently represent an oxygen atom or a sulfur atom; Xs may be
the same or different and each represent a hydrogen atom, a halogen
atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy
group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4
haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4
haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4
haloalkylsulfonyl group, a cyano group, a nitro group, an amino
group, or an amino group which may be substituted by a C1-C4 alkyl
group;
n represents an integer of 0 to 4;
Q represents a phenyl group,
[0027] a substituted phenyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a
C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano
group, a nitro group, a hydroxyl group, a pentafluorosulfanyl
group, a phenyl group, a substituted phenyl group (which may have
the same or different substituents selected from a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl
group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group,
a hydroxyl group, and a pentafluorosulfanyl group), a thienyl
group, and a substituted thienyl group (which may have the same or
different substituents selected from a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8
halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a
C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl
group, and a pentafluorosulfanyl group),
a naphthyl group,
[0028] a substituted naphthyl group having one or more substituents
which may be the same or different and which are selected from a
halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy
group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may
be substituted by at least one hydroxyl group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl
group, and a pentafluorosulfanyl group, a heterocyclic group (which
represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl
group, a pyridazyl group, a furyl group, a thienyl group, an
oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a
thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a
pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl
group, or a tetrazolyl group), a substituted heterocyclic group
(which represents a pyridyl group, a pyridine-N-oxide group, a
pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl
group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl
group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl
group, a pyrrole group, an imidazolyl group, a triazolyl group, a
pyrazolyl group, or a tetrazolyl group) having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group, a tetrahydronaphthyl group, or
[0029] a substituted tetrahydronaphthyl group having one or more
substituents which may be the same or different and which are
selected from a halogen atom, a C1-C6 alkyl group, a C1-C6
haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 haloalkyl group which may be substituted by at least one
hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a cyano group, a nitro group, a hydroxyl group, and a
pentafluorosulfanyl group (excluding a case (1) in which Q
represents 3,4-dichlorophenyl when R1 represents a methyl group, a
case (2) in which Q represents an unsubstituted phenyl group when
R1 represents an ethyl group, and a case (3) in which Q represents
an unsubstituted pyridyl group when R1 represents an unsubstituted
phenyl group).
[0030] [3] Compounds represented by formula (2) ##STR3## wherein
A.sub.1, A.sub.2, A.sub.3, A.sub.4, R.sub.1, R.sub.2, R.sub.3,
G.sub.1, G.sub.2, G.sub.3, X, and n each represent the same as in
formula [1], and Hal represents a halogen atom.
[0031] [4] Compounds represented by formula (3) ##STR4## wherein
A.sub.1, A.sub.2, A.sub.3, A.sub.4, R.sub.3, G.sub.3, X, n and Q
each represent the same as in formula [1].
[0032] [5] Compounds represented by formula (4) ##STR5## wherein
A.sub.1, A.sub.2, A.sub.3, A.sub.4, R.sub.2, R.sub.3, G.sub.3, X,
and n each represent the same as in formula [1], and Q represents a
group represented by formula (1-2) or (1-3): ##STR6## (wherein
Y.sub.1, Y.sub.2, Y.sub.4, and Y.sub.5 may be the same or different
and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a
cyano group, or a nitro group, and Y.sub.3 represents a C1-C6
haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group
which may be substituted by at least one hydroxyl group, a C1-C6
haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6
haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only
one of Y.sub.1 and Y.sub.5 represents a hydrogen atom) ##STR7##
(wherein Y.sub.6, Y.sub.7, and Y.sub.9 may be the same or different
and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a
cyano group, or a nitro group, and Y.sub.8 represents a C1-C6
haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group
which may be substituted by at least one hydroxyl group, a C1-C6
haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6
haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only
one of Y.sub.6 and Y.sub.9 represents a hydrogen atom).
[0033] [6] A method for producing the above-described compounds in
[1] comprising reacting the compounds represented in [3] by formula
(2) with compounds represented by formula (5): ##STR8## wherein
R.sub.3 and Q each represent the same as in [1].
[0034] [7] A method for producing the above-described compounds in
[1] comprising reacting the compounds represented in [4] by formula
(3) with compounds represented by formula (6): H-G.sub.2-R (6)
wherein R.sub.1 and G.sub.2 each represent the same as in [1].
[0035] [8] A method for producing the above-described compounds in
[1] comprising reacting the compounds represented in [5] by formula
(4) with compounds represented by formula (7): ##STR9## wherein
R.sub.1, G.sub.1, and G.sub.2 each represent the same as in [1]
[0036] [9] Aniline derivatives represented by formula (8):
##STR10## wherein R.sub.7 represents a C1-C6 haloalkyl group,
Y.sub.10, Y.sub.11, Y.sub.12, and Y.sub.13 may be the same or
different and each represent a hydrogen atom, a halogen atom, a
C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a
C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a
pentafluorosulfanyl group, a cyano group, or a nitro group, and
R.sub.8 and R.sub.9 independently represent a hydrogen atom, a
C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted
m-nitrobenzoyl group, and m represents 0, 1, or 2.
[0037] [10] Aniline derivatives represented by formula (9):
##STR11## wherein R.sub.10 represents a C1-C6 haloalkyl group which
may be substituted by at least one hydroxyl group, Y.sub.14,
Y.sub.15, Y.sub.16, and Y.sub.17 may be the same or different and
each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl
group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a
cyano group, or a nitro group, and R.sub.11, and R.sub.12
independently represent a hydrogen atom, a C1-C4 alkyl group, a
m-nitrobenzoyl group, or a substituted m-nitrobenzoyl group.
[0038] [11] An insecticide comprising any one of the compounds in
[1] or [2] as an active ingredient.
[0039] [12] A method for using a chemical comprising treating a
useful crop or soil with an effective amount of any one of the
compounds [1] or [2], for protecting the useful crop from harmful
organisms.
[0040] [13] A method for preventing pests comprising using the
compound [1] or [2] and at least one insecticide and/or fungicide
in combination.
[0041] The compounds of the present invention exhibit an excellent
preventive effect as insecticides in low dosages, and also exhibit
an excellent preventive effect when being used in combination with
another insecticide, an acaricide, a nematocide, a fungicide, a
herbicide, a plant growth regulator, or a biological pesticide.
BEST MODE FOR CARRYING OUT THE INVENTION
[0042] In the definitions of formula (1) of the present invention,
the term "halogen atom" means a fluorine atom, a chlorine, atom, a
bromine atom, or an iodine atom. The characters "n-", "i-", "s-",
and "t-" mean "normal", "iso", "secondary", and "tertiary",
respectively. With respect to the expression "Ca-Cb (a and b each
represent an integer of 1 or more)", for example, "C1-C6" means
that the number of carbon atoms is 1 to 6, "C3-C8" means that the
number of carbon atoms is 3 to 8, and "C1-C4" means that the number
of carbon atoms is 1 to 4.
[0043] In the definitions of the formulae such as formula (1) of
the present invention, the used terms have the following
meanings:
[0044] The term "an alkyl group which may be substituted" means a
straight, branched or cyclic alkyl group which may be substituted
by the same or different groups selected from a hydrogen atom, a
halogen atom, a hydroxyl group, a cyano group, a nitro group, a
C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio
group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a
C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6
haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6
haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6
haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino
group, a di-C1-C6 alkylamino group, a phenyl group which may be
substituted, a phenylcarbonyl group which may be substituted, a
phenylamino group which may be substituted, and a heterocyclic
group which may be substituted.
[0045] The term "an alkylcarbonyl group which may be substituted"
means a straight, branched or cyclic alkylcarbonyl group which may
be substituted by the same or different groups selected from a
hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a
nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6
alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6
alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6
alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino
group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a
phenyl group which may be substituted, a phenylcarbonyl group which
may be substituted, a phenylamino group which may be substituted,
and a heterocyclic group which may be substituted.
[0046] The term "a phenyl group which may be substituted" means a
phenyl group which may be substituted by the same or different
groups selected from a hydrogen atom, a halogen atom, a hydroxyl
group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl
group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl
group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy
group, an amino group, a C1-C6 alkylamino group, a di-C1-C6
alkylamino group, a phenyl group which may be substituted, a
phenylcarbonyl group which may be substituted, a phenylamino group
which may be substituted, and a heterocyclic group which may be
substituted.
[0047] The term "a naphthyl group which may be substituted" means a
naphthyl group which may be substituted by the same or different
groups selected from a hydrogen atom, a halogen atom, a hydroxyl
group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6
haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio
group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl
group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl
group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl
group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl
group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy
group, an amino group, a C1-C6 alkylamino group, a di-C1-C6
alkylamino group, a phenyl group which may be substituted, a
phenylcarbonyl group which may be substituted, a phenylamino group
which may be substituted, and a heterocyclic group which may be
substituted.
[0048] The term "a tetrahydronaphthyl group which may be
substituted" means a tetrahydronaphthyl group which may be
substituted by the same or different groups selected from a
hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a
nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a
C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6
alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6
alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6
alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6
alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino
group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a
phenyl group which may be substituted, a phenylcarbonyl group which
may be substituted, a phenylamino group which may be substituted,
and a heterocyclic group which may be substituted.
[0049] The term "a heterocyclic group which may be substituted"
means a heterocyclic group which may be substituted by the same or
different groups selected from a hydrogen atom, a halogen atom, a
hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group,
a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6
haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6
haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6
haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6
haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino
group, a di-C1-C6 alkylamino group, a phenyl group which may be
substituted, a phenylcarbonyl group which may be substituted, a
phenylamino group which may be substituted, and a heterocyclic
group which may be substituted.
[0050] The term "a C1-C6 alkyl group" means a straight or branched
alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl,
n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl,
neopentyl, 4-methyl-2-pentyl, n-hexyl, or 3-methyl-n-pentyl. The
term "a C1-C6 haloalkyl group" means a straight or branched alkyl
group having 1 to 6 carbon atoms and substituted by one or more
halogen atoms which may be the same or different, such as
trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl,
heptafluoro-1-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl,
1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl,
1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl,
2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl,
3,3,3-trifluoro-n-propyl, 4,4,4-trifluoro-n-butyl,
1,1,1,3,3,3-hexafluoro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl,
1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl,
1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl,
1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl,
1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl,
2,2,3,3,3-pentafluoro-n-propyl, 3,3,4,4,4-pentafluoro-2-butyl,
nonafluoro-n-butyl, nonafluoro-2-butyl, 2-fluoroethyl,
2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 3-fluoro-n-propyl,
3-chloro-n-propyl, or 3-bromo-n-propyl.
[0051] The term "a C2-C6 alkenyl group" means an alkenyl group
having 2 to 6 carbon atoms and a double bond in its carbon chain,
such as vinyl, allyl, 2-butenyl, or 3-butenyl. The term "a C2-C6
haloalkenyl group" means a straight or branched alkenyl group
having 2 to 6 carbon atoms and a double bond in its carbon chain
and substituted by one or more halogen atoms which may be the same
or different, such as 3,3-difluoro-2-propenyl,
3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl,
2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, or
3,4,4-tribromo-3-butenyl.
[0052] The term "a C2-C6 alkynyl group" means an alkynyl group
having 2 to 6 carbon atoms and a triple bond in its carbon chain,
such as propargyl, 1-butyne-3-yl, or 1-butyne-3-methyl-3-yl. The
term "a C2-C6 haloalkenyl group" means a straight or branched
alkyenyl group having 2 to 6 carbon atoms and a triple bond in its
carbon chain and substituted by one or more halogen atoms which may
be the same or different.
[0053] The term "a C3-C8 cycloalkyl group" means a cycloalkyl group
having 3 to 8 carbon atoms and a cyclic structure, such as
cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl,
3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl,
3-methylcyclohexyl, or 4-methylcyclohexyl. The term "a C3-C8
halocycloalkyl group" means a cycloalkyl group having 3 to 8 carbon
atoms and a cyclic structure and substituted by one or more halogen
atoms which may be the same or different, such as
2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, or
4-chlorocyclohexyl.
[0054] The term "a C1-C6 alkoxy group" means a straight or branched
alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy,
n-propyloxy, isopropyloxy, n-butoxy, s-butoxy, i-butoxy, or
t-butoxy. The term "a C1-C6 haloalkoxy group" means a straight or
branched haloalkoxy group having 1 to 6 carbon atoms and
substituted by one or more halogen atoms which may be the same or
different, such as trifluoromethoxy, pentafluoroethoxy,
heptafluoro-n-propyloxy, heptafluoro-1-propyloxy,
1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy,
2-chloroethoxy, or 3-fluoro-n-propyloxy.
[0055] The term "a C1-C6 alkylthio group" means a straight or
branched alkylthio group having 1 to 6 carbon atoms, such as
methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio,
s-butylthio, or t-butylthio. The term "a C1-C6 haloalkylthio group"
means a straight or branched alkylthio group having 1 to 6 carbon
atoms and substituted by one or more halogen atoms which may be the
same or different, such as trifluoromethylthio,
pentafluoroethylthio, 2,2,2-trifluoroethylthio,
heptafluoro-n-propylthio, heptafluoro-1-propylthio,
nonafluoro-n-butylthio, or nonafluoro-2-butylthio.
[0056] The term "a C1-C6 alkylsulfinyl group" means a straight or
branched alkylsulfinyl group having 1 to 6 carbon atoms, such as
methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl,
n-butylsulfinyl, s-butylsulfinyl, or t-butylsulfinyl. The term "a
C1-C6 haloalkylsulfinyl group" means a straight or branched
alkylsulfinyl group having 1 to 6 carbon atoms and substituted by
one or more halogen atoms which may be the same or different, such
as trifluoromethylsulfinyl, pentafluoroethylsulfinyl,
2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl,
heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, or
nonafluoro-2-butylsulfinyl.
[0057] The term "a C1-C6 alkylsulfonyl group" means a straight or
branched alkylsulfonyl group having 1 to 6 carbon atoms, such as
methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl,
n-butylsulfonyl, s-butylsulfonyl, or t-butylsulfonyl. The term "a
C1-C6 haloalkylsulfonyl group" means a straight or branched
alkylsulfonyl group having 1 to 6 carbon atoms and substituted by
one or more halogen atoms which may be the same or different, such
as trifluoromethylsulfonyl, pentafluoroethylsulfonyl,
2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl,
heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, or
nonafluoro-2-butylsulfonyl.
[0058] The term "a C1-C4 alkylcarbonyl group" means a straight,
branched, or cyclic alkylcarbonyl group having 1 to 4 carbon atoms,
such as acetyl, propionyl, isopropylcarbonyl, or
cyclopropylcarbonyl. The term "a C1-C4 haloalkylcarbonyl group"
means a straight or branched alkylcarbonyl group having 1 to 4
carbon atoms and substituted by one or more halogen atoms which may
be the same or different, such as trifluoroacetyl,
pentafluoropropionyl, trichloroacetyl, chloroacetyl, bromoacetyl,
or 3-chloropropionyl.
[0059] The term "a C1-C4 alkoxycarbonyl group" means a straight or
branched alkoxycarbonyl group having 1 to 4 carbon atoms, such as
methoxycarbonyl, ethoxycarbonyl, or isopropyloxycarbonyl.
[0060] The term "a C1-C4 alkylcarbonyloxy group" means a straight
or branched alkylcarbonyloxy group having 1 to 4 carbon atoms, such
as acetoxy or propionyloxy. The term "a C1-C4 alkylsulfonyloxy
group" means a straight or branched alkylsulfonyloxy group having 1
to 4 carbon atoms, such as methylsulfonyloxy. The term "a C1-C4
haloalkylsulfonyloxy group" means a straight or branched
alkylsulfonyloxy group having 1 to 4 carbon atoms and substituted
by one or more halogen atoms which may be the same or different,
such as trifluoromethylsulfonyloxy or
pentafluoroethylsulfonyloxy.
[0061] The term "a C1-C4 alkylene group" means a straight or
branched alkylene group having 1 to 4 carbon atoms, such as
methylene, ethylene, propylene, dimethylmethylene, or isobutylene.
The term "a C2-C4 alkenylene group" means a straight or branched
alkenylene group having 2 to 4 carbon atoms and a double bond in
its carbon chain. The term "a C3-C4 alkynylene group" means a
straight or branched alkynylene having 3 to 4 carbon atoms and a
triple bond in its carbon chain. The term "a C1-C4 haloalkylene
group" means a straight or branched alkylene group having 1 to 4
carbon atoms and substituted by one or more halogen atoms which may
be the same or different, such as chloromethylene, chloroethylene,
dichloromethylene, or difluoromethylene.
[0062] The term "a C2-C4 haloalkenylene group" means a straight or
branched alkynylene having 2 to 4 carbon atoms and a double bond in
its carbon chain, and substituted by one or more halogen atoms
which may be the same or different. The term "a C3-C4
haloalkynylene group" means a straight or branched alkynylene group
having 3 to 4 carbon atoms and a triple bond in its carbon chain,
and substituted by one or more halogen atoms which may be the same
or different.
[0063] The term "a C1-C6 haloalkyl group which may be substituted
by one ore more hydroxyl groups" means a straight or branched alkyl
group having 1 to 6 carbon atoms and one or more hydroxyl groups in
its carbon chain, and substituted by one or more halogen atoms
which may be the same or different, such as
1,2,2,2-tetrafluoro-1-hydroxyethyl,
1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl,
1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl,
1,2,2,3,3,4,4,4-octafluoro-1-hydroxy-n-butyl, or
1,3-dichloro-1,1,3,3-tetrafluoro-2-hydroxy-2-propyl.
[0064] The term "a substituted m-nitrobenzoyl group" means a
m-nitrobenzoyl group having one or more substituents, such as
2-fluoro-3-nitrobenzoyl, 4-fluoro-3-nitrobenzoyl,
2-fluoro-5-nitrobenzoyl, or 4-chloro-3-nitrobenzoyl.
[0065] The compounds represented by formula (1) of the present
invention may contain at least one asymmetric carbon atom or
asymmetric center and thus have at least two types of optical
isomers. The present invention includes the optical isomers and
mixtures thereof at any proportions. The compounds represented by
formula (1) of the present invention may contain at least two types
of geometric isomers derived from carbon-carbon double bonds in the
structural formulae. The present invention also includes the
geometric isomers and mixtures thereof at any proportions.
[0066] Preferred examples of the substituents or atoms in the
compounds represented by the formulae such as formula (1) of the
present invention include the following:
[0067] Preferably, R.sub.1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
alkenyl, C2-C6 haloalkenyl, a C2-C6 alkynyl, C2-C6 haloalkynyl,
C3-C8 cycloalkyl, C3-C8 halocycloalkyl, -E.sub.1-Z.sub.1-R.sub.4
(wherein E.sub.1 represents C1-C4 alkylene, C2-C4 alkenylene, C3-C4
alkynylene, C1-C4 haloalkylene, C2-C4 haloalkenylene, or C3-C4
haloalkynylene, R.sub.4 represents a hydrogen atom, C1-C6 alkyl,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl,
or C2-C6 haloalkynyl, and Z.sub.1 represents --O--, --S--, --SO--,
or --SO.sub.2--), or -E.sub.2-R.sub.6 (wherein E.sub.2 represents
C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl, C2-C4
haloalkenyl, or C3-C4 haloalkynyl, and R.sub.6 represents C3-C8
cycloalkyl, C3-C8 halocycloalkyl, cyano, nitro, hydroxyl, phenyl,
substituted phenyl having one or more substituents which may be the
same or different and which are selected from halogen, C1-C6 alkyl,
C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio,
C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl,
C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, cyano, nitro,
hydroxyl, C1-C4 alkylcarbonyl, C1-C4 haloalkylcarbonyl, C1-C4
alkylcarbonyloxy, and C1-C4 alkoxycarbonyl, pyridyl, or substituted
pyridyl having one or more substituents selected from halogen,
C1-C6 haloalkyl, and C1-C6 haloalkoxy). More preferably, R.sub.1 is
C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C8
halocycloalkyl, -E.sub.1-Z.sub.1-R.sub.4 (wherein E.sub.1
represents C1-C4 alkylene or C1-C4 haloalkylene, R.sub.4 represents
C1-C6 alkyl or C1-C6 haloalkyl, and Z.sub.1 represents --O--,
--S--, --SO--, or --SO.sub.2--), or -E.sub.2-R.sub.6 (wherein
E.sub.2 represents C1-C4 alkyl, R.sub.6 represents C3-C8
cycloalkyl, cyano, substituted phenyl having one or more
substituents which may be the same or different and which are
selected from halogen, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6
haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl,
cyano, and nitro, pyridyl, substituted pyridyl having one or more
substituents selected from halogen, C1-C6 haloalkyl, and C1-C6
haloalkoxy, thienyl, or tetrahydrofuryl).
[0068] Preferably, R.sub.2 and R.sub.3 are independently hydrogen
or C1-C4 alkyl, and more preferably hydrogen, methyl, or ethyl.
[0069] Preferably, G.sub.1, G.sub.2, and G.sub.3 are independently
oxygen or sulfur, and more preferably oxygen.
[0070] Preferably, X is hydrogen, halogen or trifluoromethyl, and
more preferably hydrogen or fluorine.
[0071] Preferably, n is 0 or 1.
[0072] Preferably, Q is phenyl, substituted phenyl having one or
more substituents selected from halogen, C1-C6 alkyl, C1-C6
haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl which
may be substituted by one or more hydroxyl groups, C1-C6 alkylthio,
C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl,
C1-C6 alkylsulfonyl, pentafluorosulfanyl, cyano, and nitro,
pyridyl, or substituted pyridyl having one or more substituents
selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy,
C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one
or more hydroxyl groups, C1-C6 alkylthio, C1-C6 haloalkylthio,
C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl,
C1-C6 haloalkylsulfonyl, pentafluorosulfanyl, cyano, and nitro.
More preferably, Q is substituted phenyl or substituted pyridyl
represented by formula (1-2) or (1-3). In the formula, preferably,
Y.sub.1 and Y.sub.5 are independently hydrogen, C1-C4 alkyl,
halogen, or methylthio, and only one of Y.sub.1 and Y.sub.5
represents a hydrogen atom.
[0073] Preferably, Y.sub.2 and Y.sub.4 are each hydrogen.
[0074] Preferably, Y.sub.3 is C1-C6 haloalkyl, C1-C6 haloalkoxy,
C1-C6 haloalkyl which may be substituted by one or more hydroxyl
groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6
haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y.sub.3
is C1-C6 haloalkyl, C1-C6 haloalkyl which may be substituted by one
or more hydroxyl group, C1-C6 haloalkylthio, C1-C6
haloalkylsulfinyl, or C1-C6 haloalkylsulfonyl.
[0075] Preferably, Y.sub.6 and Y.sub.9 are independently hydrogen,
C1-C4 alkyl, halogen, or methylthio, and only one of Y.sub.6 and
Y.sub.9 represents a hydrogen atom.
[0076] Preferably, Y.sub.7 is hydrogen.
[0077] Preferably, Y.sub.8 is C1-C6 haloalkyl, C1-C6 haloalkoxy,
C1-C6 haloalkyl which may be substituted by one or more hydroxyl
groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6
haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y.sub.8
is C1-C6 haloalkyl or C1-C6 haloalkoxy.
[0078] Preferably, Hal is chlorine.
[0079] Preferably, R.sub.7 is C1-C6 haloalkyl, and more preferably
R.sub.7 is C1-C6 alkyl substituted by fluorine, such as
pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,
nonafluoro-n-butyl, or nonafluoro-2-butyl.
[0080] Preferably, Y.sub.10 and Y.sub.13 are independently
hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of
Y.sub.10 and Y.sub.13 represents a hydrogen atom. More preferably,
Y.sub.10 and Y.sub.13 are each chlorine, bromine, or methyl.
[0081] Preferably, Y.sub.11, and Y.sub.12 are each hydrogen.
[0082] Preferably, R.sub.8 and R.sub.9 are each hydrogen, C1-C4
alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl, and only one of
R.sub.8 and R.sub.9 represent C1-C4 alkyl, m-nitrobenzoyl, or
2-fluoro-3-nitrobenzoyl.
[0083] Preferably, m is 0, 1, or 2.
[0084] Preferably, R.sub.10 is 1,2,2,2-tetrafluoro-1-hydroxyethyl,
1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl,
1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl,
1,2,2,3,3,4,4,4-octafluoro-1-hydroxy-n-butyl, or
1,3-dichloro-1,1,3,3-tetrafluoro-2-hydroxy-2-propyl, and more
preferably, R.sub.10 is
1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl.
[0085] Preferably, Y.sub.14 and Y.sub.17 are independently
hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of
Y.sub.14 and Y.sub.17 represents a hydrogen atom. More preferably,
none of Y.sub.14 and Y.sub.17 represents a hydrogen atom.
[0086] Preferably, Y.sub.15 and Y.sub.16 are each hydrogen.
[0087] Preferably, R.sub.11 and R.sub.12 are each hydrogen, C1-C4
alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl, and only one of
R.sub.11 and R.sub.12 represents C1-C4 alkyl, m-nitrobenzoyl, or
2-fluoro-3-nitrobenzoyl.
[0088] Representative processes for producing the compounds of the
present invention will be described below. Although the compounds
of the present invention can be produced according to the methods,
the production processes are not limited to the processes described
below.
[0089] An embodiment of the representative processes for producing
the compounds of the present invention is Production Method 1 (in
the formula, R.sub.1, R.sub.3, G.sub.1, G.sub.2, (X)n, and Q
represent the same as described above). ##STR12## 1-(i) Formula
(10) .fwdarw.Formula (12)
[0090] A m-nitrobenzoyl chloride derivative represented by formula
(10) is reacted with an aromatic amine derivative represented by
formula (11) in an appropriate solvent to produce a benzamide
derivative represented by formula (12). In this step, an
appropriate base can also be used. As the solvent, any solvent
which does not significantly inhibit the progress of reaction can
be used. Examples of the solvent include aromatic hydrocarbons such
as benzene, toluene, and xylene; halogenated hydrocarbons such as
dichloromethane, chloroform, and carbon tetrachloride; chained or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitrites such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. Examples of
the base include organic bases such as triethylamine,
tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali
metal hydroxides such as sodium hydroxide and potassium hydroxide;
carbonates such as sodium hydrogen carbonate and potassium
carbonate; phosphates such as dipotassium hydrogen phosphate and
trisodium phosphate; alkali metal hydrides such as sodium hydride;
and alkali metal alcoholates such as sodium methoxide and sodium
ethoxide. The base may be used in an appropriate amount in the
range of molar equivalents of 0.01 to 5 times the amount of the
compound represented by formula (10). The reaction temperature may
be appropriately determined in the range of -20.degree. C. to the
reflux temperature of the solvent used, and the reaction time may
be appropriately determined in the range of several minutes to 96
hours. The m-nitrobenzoyl chloride derivative represented by
formula (10) can be easily produced from a m-nitrobenzoic acid
derivative by a conventional method using a halogenating agent.
Examples of the halogenating agent include thionyl chloride,
thionyl bromide, phosphorus oxychloride, oxalyl chloride, and
phosphorus trichloride. In a process for producing the compound
represented by formula (12) using the m-nitrobenzoic acid
derivative and the compound represented by formula (11) without
using a halogenating agent, 1-hydroxybenzotriazole functioning as
an additive, and N,N'-dicyclohexyl carbodiimide functioning as a
condensing agent can be used according to the technique disclosed
in, for example, Chem. Ber. p. 788 (1970). Other examples of the
condensing agent include 1-ethyl-3-(3-dimethylaminopropyl)
carbodiimide and 1,1'-carbonyl-bis-1H-imidazole. Alternatively, the
compound represented by formula (12) can be produced by a mixed
acid anhydride technique using a chloroformic acid ester according
to the technique disclosed in J. Am. Chem. Soc. p. 5012 (1967).
Examples of the chloroformic acid ester include isobutyl
chloroformate and isopropyl chloroformate. Instead of the
chloroformic acid ester, diethylacetyl chloride or trimethylacetyl
chloride can be used. In the technique using the condensing agent
and the mixed acid anhydride technique, the solvent, the reaction
temperature, and the reaction time are not limited to those
disclosed in the above documents, and an inert solvent which does
not inhibit the progress of reaction may be appropriately used.
Also, the reaction temperature and the reaction time may be
appropriately selected according to the progress of reaction.
1-(ii) Formula (12) .fwdarw.Formula (13)
[0091] The benzamide derivative having a nitro group represented by
formula (12) can be converted to a benzamide derivative having an
amino group represented by formula (13) by reduction reaction.
Examples of a technique for the reduction reaction include a
technique using hydrogenation and a technique using tin(II)
chloride (anhydride). In the former technique, reaction can be
performed in a hydrogen atmosphere in the presence of a catalyst in
a proper solvent under normal pressure or high pressure. Examples
of the catalyst include palladium catalysts such as
palladium-carbon, nickel catalysts such as Raney nickel, cobalt
catalysts, ruthenium catalysts, rhodium catalysts, and platinum
catalysts. Examples of the solvent include water, alcohols such as
methanol and ethanol; aromatic hydrocarbons such as benzene and
toluene; chained or cyclic ethers such as ethers, dioxane, and
tetrahydrofuran; and esters such as ethyl acetate. The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflux temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours. As a result, the compound represented
by formula (13) can be produced. In the latter technique, the
conditions are not limited, and the compound represented by formula
(13) can be produced under the conditions described in, for
example, Organic Syntheses, Coll. Vol. III, p. 453.
1-(iii) Formula (13) .fwdarw.Formula (14)
[0092] The benzamide derivative having a amino group represented by
formula (13) is reacted with a compound represented by formula (7)
(for example, a chloroformic ester, a chlorothioformic ester, or a
chlorodiformic thioester) in a proper solvent to produce a compound
represented by formula (14) of the present invention. In this step,
an appropriate base can also be used. As the solvent, any solvent
which does not significantly inhibit the progress of reaction can
be used. Examples of the solvent include aromatic hydrocarbons such
as benzene, toluene, and xylene; halogenated hydrocarbons such as
dichloromethane, chloroform, and carbon tetrachloride; chained or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitrites such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. Examples of
the base include organic bases such as triethylamine,
tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali
metal hydroxides such as sodium hydroxide and potassium hydroxide;
carbonates such as sodium hydrogen carbonate and potassium
carbonate; phosphates such as dipotassium hydrogen phosphate and
trisodium phosphate; alkali metal hydrides such as sodium hydride;
and alkali metal alcoholates such as sodium methoxide and sodium
ethoxide. The base may be used in an appropriate amount in the
range of molar equivalents of 0.01 to 5 times the amount of the
compound represented by formula (13). The reaction temperature may
be appropriately determined in the range of -20.degree. C. to the
reflux temperature of the solvent used, and the reaction time may
be appropriately determined in the range of several minutes to 96
hours.
[0093] A compound represented by formula (16) of the present
invention can be produced by Production Method 2 (in the formula,
R.sub.1, R.sub.3, G.sub.2, (X)n, and Q represent the same as
described above) using a 3-isocyanatobenzoly chloride represented
by formula (15) as a starting material, an alcohol represented by
formula (6), a thiol, and an aromatic amine represented by formula
(11) according to the technique disclosed in J. Org. Chem., p. 142
(1966). ##STR13##
[0094] In this step, a solvent can be used. As the solvent, any
solvent other than the solvents described in the above document can
be used as long as it does not significantly inhibit the progress
of reaction. Examples of the solvent include aromatic hydrocarbons
such as benzene, toluene, and xylene; halogenated hydrocarbons such
as dichloromethane, chloroform, and carbon tetrachloride; chained
or cyclic ethers such as dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitriles such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. Also, a base
may be added for accelerating the reaction. Examples of the base
other than those disclosed in the above document include organic
bases such as triethylamine, pyridine, and 4-dimethylaminopyridine;
and inorganic bases such as potassium carbonate. The base may be
used in an appropriate amount in the range of molar equivalents of
0.01 to 5 times the amount of the compound represented by formula
(15). The reaction temperature may be appropriately determined in
the range of -20.degree. C. to the reflux temperature of the
solvent used, and the reaction time may be appropriately determined
in the range of several minutes to 96 hours.
[0095] A thioamide compound can be produced from a compound
represented by formula (17) using a Lawson reagent according
Production Method 3 (in the formula, R.sub.1, R.sub.2, R.sub.3,
G.sub.1, G.sub.2, (X)n, and Q represent the same as described
above). ##STR14## 3-(i) Formula (17) .fwdarw.Formula (18)
[0096] The reaction can be performed under the conditions described
in Synthesis, p. 463 (1993) and Synthesis, p. 829 (1984), but the
conditions such as a solvent are not limited to those described in
these documents.
3-(ii) Formula (18) .fwdarw.Formula (19)
[0097] A compound represented by formula (19) of the present
invention can be produced using a compound represented by formula
(7) (for example, a chloroformic ester or a chlorothioformic ester)
under the conditions properly selected from the reaction conditions
described above in the step 1-(iii) of Production Method 1.
[0098] A chloropyridinecarboxylic acid can be used as a starting
material. For example, a compound represented by formula (23) can
be produced from a chloropyridinecarboxylic acid represented by
formula (20) according to Production Method 4 (in the formula,
R.sub.1, R.sub.2, R.sub.3, Q, G.sub.1, and G.sub.2 represent the
same as described above) ##STR15## 4-(i) Formula (20)
.fwdarw.Formula (21)
[0099] A compound represented by formula (18) is halogenated in the
presence or absence of an inert solvent and then reacted with an
aromatic amine represented by formula (11) to produce a compound
represented by formula (21). As the solvent usable in the
halogenation step, any solvent which does not significantly inhibit
the progress of reaction can be used. Examples of the solvent
include aromatic hydrocarbons such as benzene, toluene, and xylene;
halogenated hydrocarbons such as dichloromethane, chloroform, and
carbon tetrachloride; chained or cyclic ethers such as diethyl
ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters
such as ethyl acetate and butyl acetate; ketones such as acetone,
methyl isobutyl ketone, and cyclohexanone; amides such as
dimethylformamide and dimethylacetamide; nitriles such as
acetonitrile; and inert solvents such as
1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or
in a mixture of two ore more kinds. Examples of a halogenating
agent include thionyl chloride, thionyl bromide, phosphorus
oxychloride, oxalyl chloride, and phosphorus trichloride. The
amount of the halogenating agent used may be appropriately
determined in the range of molar equivalents of 1 to 10 times the
amount of the compound represented by formula (20). Also,
N,N-dimethylformamide may be added as an auxiliary for accelerating
the reaction. The reaction temperature may be appropriately
determined in the range of -20.degree. C. to the reflux temperature
of the solvent used, and the reaction time may be appropriately
determined in the range of several minutes to 96 hours. As the
solvent usable in the amidation step, any solvent which does not
significantly inhibit the progress of reaction can be used.
Examples of the solvent include aromatic hydrocarbons such as
benzene, toluene, and xylene; halogenated hydrocarbons such as
dichloromethane, chloroform, and carbon tetrachloride; chained or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitrites such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. Also, a base
may be added for accelerating the progress of reaction. Examples of
the base include organic bases such as triethylamine, pyridine,
4-dimethylaminopyridine; and inorganic bases such as potassium
carbonate. The amount of the base used may be appropriately
determined in the range of molar equivalents of 0.01 to 5 times the
amount of the compound represented by formula (11). The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflux temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours.
[0100] A process for producing a compound represented by formula
(21) from a compound represented by formula (20) and a compound
represented by formula (11) without using a halogenating agent is
presented by a process according to the technique disclosed in, for
example, Chem. Ber., p. 788 (1970) where 1-hydroxybenzotriazole as
an additive and N,N'-dicyclohexyl carbodiimide as a condensing
agent are used, respectively. Other examples of the condensing
agent include 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, and
1,1'-carbonyl-bis-1H-imidazole. The compound represented by formula
(21) can also be produced by a mixed acid anhydride technique using
a chloroformic ester according to the technique disclosed in J. Am.
Chem. Soc., p. 5012 (1967). Examples of a chloroformic ester
include isobutyl chloroformate and isopropyl chloroformate. A
compound other than a chloroformic ester, for example,
diethylacetyl chloride or trimethylacetyl chloride, can also be
used. In the technique using the condensing agent and the mixed
acid anhydride technique, the solvent, the reaction temperatures,
and the reaction times are not limited to those disclosed in the
above documents, and an inert solvent which does not significantly
inhibit the progress of reaction may be appropriately used. Also,
the reaction temperature and the reaction time may be appropriately
selected according to the progress of reaction.
4-(ii) Formula (21) .fwdarw.Formula (22)
[0101] A compound represented by formula (22) can be produced by
amination with ammonia according to the conditions described in,
for example, J. Org. Chem., p. 280 (1958). The conditions such as
the reaction solvent are not limited to those disclosed in the
above document, and an inert solvent which does not significantly
inhibit the progress of reaction may be appropriately used. Also,
the reaction temperature and the reaction time may be appropriately
selected according to the progress of reaction. As an aminating
agent, methylamine or ethylamine can be used instead of
ammonia.
4-(iii) Formula (22) .fwdarw.Formula (23)
[0102] A compound represented by formula (23) of the present
invention can be produced by using a compound represented by
formula (7) (for example, a chloroformic ester or a
chlorothioformic ester) under the conditions appropriately selected
from the reaction conditions described above in the step
1-(iii) of Production Method 1.
[0103] Even when another nitrogen-containing aromatic carboxylic
acid such as 4-chloropyridine-2-carboxlic acid or
6-chloropyridine-2-carboxylic acid is selected as a starting
material, the compound of the present invention can be produced
according to Production Method 4. In the use of the former starting
material, a compound represented by formula (1) wherein A.sub.1 is
a nitrogen atom, and A.sub.2, A.sub.3, and A.sub.4 are each a
carbon atom can be produced. In the use of the latter starting
material, a compound represented by formula (1) wherein A.sub.1,
A.sub.2, and A.sub.3 are each a carbon atom, and A.sub.4 is a
nitrogen atom can be produced.
[0104] The compound represented by formula (23) is reacted with an
appropriate oxidizing agent to produce a corresponding
pyridine-N-oxide derivative according to the conditions disclosed
in, for example, J. Org. Chem., p. 8576 (1999). Examples of the
oxidizing agent include organic peroxy acids such as
m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen
peroxide; ozone; selenium dioxide, chromic acid; dinitrogen
tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide;
iodosylbenzene; and t-butyl hypochlorite. The solvent used in this
step is not limited to those disclosed in the above document, and
any solvent which does not significantly inhibit the progress of
reaction may be used. The solvents can be used alone or in a
mixture of one or more kinds. In particular, a polar solvent is
preferred. The reaction temperature may be appropriately determined
in the range of -20.degree. C. to the reflux temperature of the
solvent used, and the reaction time may be appropriately determined
in the range of several minutes to 96 hours.
[0105] A compound represented by formula (27) of the present
invention can be produced from a easily available m-aminobenzoic
ester derivative presented by formula (24) according to Production
Method 5 (in the formula, R.sub.1, R.sub.2, R.sub.3, G.sub.1,
G.sub.2, (X)n, and Q represent the same as described above, and R
represents a lower alkyl group). ##STR16## 5-(i) Formula (24)
.fwdarw.Formula (25)
[0106] A compound represented by formula (25) can be produced by
using a compound represented by formula (7) (for example, a
chloroformic ester or a chlorothioformic ester) under the
conditions appropriately selected from the reaction conditions
described above in the step 1-(iii) of Production Method 1.
5-(ii) Formula (25) .fwdarw.Formula (26)
[0107] A compound represented formula (26) can be produced by
hydrolysis with an alkali metal hydroxide such as sodium hydroxide
or potassium hydroxide, an alkali earth metal hydroxide such as
calcium hydroxide, or an inorganic acid such as hydrochloric acid
or sulfuric acid according to a conventional technique.
5-(iii) Formula (26) .fwdarw.Formula (27)
[0108] A compound represented by formula (27) of the present
invention can be produced by condensation reaction under
appropriate conditions according to the technique described above
in the step 4-(i) of Production Method 4. Among the techniques
described in the step 4-(i), in the technique using a halogenating
agent, the compound represented by formula (27) can be produced
through a compound represented by formula (2): ##STR17## (wherein
A.sub.1, A.sub.2, A.sub.3, A.sub.4, G.sub.1, G.sub.2, G.sub.3,
(X)n, and Hal each represent the same as described above). The
halogenation step and the amidation step can be performed under
reaction conditions according to the technique described above in
the step 4-(i).
[0109] The compound represented by formula (27) of the present
invention can be produced from a m-aminobenzoic acid ester
represented by formula (28) according to Production Method 6 below
(in the formula, R.sub.1, R.sub.2, R.sub.3, G.sub.1, G.sub.2, (X)n,
and Q each represent the same as described above, R represents a
lower alkyl group, and L represents a functional group having
leaving ability, such as halogen, methanesulfonyloxy, or
trifluoromethanesulfonyloxy). ##STR18## 6-(i) Formula (28)
.fwdarw.Formula (29)
[0110] A compound represented formula (29) can be produced by the
technique described above in the step 1-(iii) of Production Method
1 using a compound represented by formula (7) (for example, a
chloroformic ester or a chlorothioformic ester) under appropriate
conditions.
6-(ii) Formula (29) .fwdarw.Formula (25)
[0111] In this step, examples of a compound represented by formula
(30) include alkyl halides such as methyl iodide and ethyl iodide;
toluenesulfonic esters; methanesulfonic esters; and alkylating
agents such as dimethyl sulfate. As a solvent, any solvent which
does not significantly inhibit the progress of reaction can be
used. Examples of the solvent include aromatic hydrocarbons such as
benzene, toluene, and xylene; halogenated hydrocarbons such as
dichloromethane, chloroform, and carbon tetrachloride; chained or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitrites such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. Also, a base
may be added for accelerating the progress of reaction. Examples of
the base include organic bases such as triethylamine, pyridine, and
4-dimethylaminopyridine; inorganic bases such as potassium
carbonate, sodium hydroxide, and potassium hydroxide; and alkali
metal hydrides such as sodium hydride. The amount of the base used
may be appropriately determined in the range of molar equivalents
of 0.01 to 5 times the amount of the compound represented by
formula (29). The reaction temperature may be appropriately
determined in the range of -20.degree. C. to the reflux temperature
of the solvent used, and the reaction time may be appropriately
determined in the range of several minutes to 96 hours.
6-(iii) Formula (25) .fwdarw.Formula (27)
[0112] A compound represented by formula (27) of the present
invention can be produced by the techniques described above in the
steps 5-(ii) and 5-(iii) of Production Method 5 under appropriate
conditions.
[0113] A compound represented by formula (31) of the present
invention can be produced according to Production Method 7 (in the
formula, A.sub.1, A.sub.2, A.sub.3, A.sub.4, R.sub.1, R.sub.3,
G.sub.2, G.sub.3, and (X)n each represent the same as described
above). ##STR19##
[0114] In this step, an appropriate solvent may be used. As the
solvent, any solvent which does not significantly inhibit the
progress of reaction can be used. Examples of the solvent include
aromatic hydrocarbons such as benzene, toluene, and xylene;
halogenated hydrocarbons such as dichloromethane, chloroform, and
carbon tetrachloride; chained or cyclic ethers such as diethyl
ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters
such as ethyl acetate and butyl acetate; ketones such as acetone,
methyl isobutyl ketone, and cyclohexanone; amides such as
dimethylformamide and dimethylacetamide; nitriles such as
acetonitrile; and inert solvents such as
1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or
in a mixture of two ore more kinds. Also, an appropriate base may
be used. Examples of the base include organic bases such as
triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine;
alkali metal hydroxides such as sodium hydroxide and potassium
hydroxide; carbonates such as sodium hydrogen carbonate and
potassium carbonate; alkali metal hydrides such as sodium hydride;
and alkali metal alcoholates such as sodium methoxide and sodium
ethoxide. The amount of the base used may be appropriately
determined in the range of molar equivalents of 0.01 to 5 times the
amount of the compound represented by formula (6). The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflux temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours.
[0115] An isocyanate compound represented by formula (3) can be
produced by Production Method 8 (in the formula, A.sub.1, A.sub.2,
A.sub.3, A.sub.4, G.sub.3, R.sub.3, (X)n, and Q each represent the
same as described above) using a m-aminobenzamide derivative or a
m-aminopyridinecarboxamide derivative represented by formula (32)
as a starting material. ##STR20##
[0116] In this step, reaction can be performed by using phosgene
according to the technique described in Organic Syntheses, Coll.,
Vol. II, p. 453. An isocyanate compound represented by formula (3)
can also be produced by using a phosgene dimmer, triphosgene, or
oxalyl chloride instead of phosgene. In this step, an appropriate
solvent may be used. As the solvent, any solvent which does not
significantly inhibit the progress of reaction can be used.
Examples of the solvent include aromatic hydrocarbons such as
benzene, toluene, and xylene; halogenated hydrocarbons such as
dichloromethane, chloroform, and carbon tetrachloride; chained or
cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and
1,2-dimethoxyethane; esters such as ethyl acetate and butyl
acetate; ketones such as acetone, methyl isobutyl ketone, and
cyclohexanone; amides such as dimethylformamide and
dimethylacetamide; nitrites such as acetonitrile; and inert
solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can
be used alone or in a mixture of two ore more kinds. The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflux temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours.
[0117] An isocyanate compound represented by formula (3) can also
be produced by Production Method 9 (in the formula, A.sub.1,
A.sub.2, A.sub.3, A.sub.4, G.sub.3, R.sub.3, (X)n, and Q each
represent the same as described above) utilizing Curtius
rearrangement reaction with an isophthaloyl chloride derivative
represented by formula (33) used as a starting material according
to the technique described in Macromolecules, p. 1046 (1998).
##STR21##
[0118] In this step, an appropriate solvent may be used. As the
solvent, any solvent which does not significantly inhibit the
progress of reaction can be used. Examples of the solvent include
aromatic hydrocarbons such as benzene, toluene, and xylene;
halogenated hydrocarbons such as dichloromethane, chloroform, and
carbon tetrachloride; chained or cyclic ethers such as diethyl
ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters
such as ethyl acetate and butyl acetate; ketones such as acetone,
methyl isobutyl ketone, and cyclohexanone; amides such as
dimethylformamide and dimethylacetamide; nitrites such as
acetonitrile; and inert solvents such as
1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or
in a mixture of two ore more kinds. The reaction temperature may be
appropriately determined in the range of -20.degree. C. to the
reflux temperature of the solvent used, and the reaction time may
be appropriately determined in the range of several minutes to 96
hours. In producing a compound represented formula (34), ethanol,
propanol, or benzyl alcohol can be used as an alcohol. In
esterolysis, hydrolysis or catalytic hydrogen reduction can be
performed by a conventional technique.
[0119] An aniline derivative represented by formula (39) can be
produced by using an aminothiophenol derivative as a starting
material according Production Method 10 (in the formula, R.sub.7,
Y.sub.11, Y.sub.12, and m each represent the same as described
above, Y.sub.10 and Y.sub.13 each represent a hydrogen atom or a
halogen atom except a case in which both groups are hydrogen atoms
as far as this Method is concerned, Y.sub.10a and Y.sub.13a each
represent a hydrogen atom, a halogen atom, or a methyl group as far
as this Method is concerned, and one of Y.sub.10a and Y.sub.13a
necessarily represents a methyl group). ##STR22## 10-(i) Formula
(35) .fwdarw.Formula (37)
[0120] A compound represented by formula (38) can be produced by
reaction of aminothiophenol represented by formula (35) with a
haloalkyl iodide represented by formula (36) according to the
method described in J. Fluorine Chem., p. 207 (1994).
[0121] Examples of a haloalkyl iodide represented by formula (36)
include trifluoromethyl iodide, pentafluoroethyl iodide,
heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide,
nonafluoro-n-butyl iodide, and nonafluoroisopropyl iodide. The
amount of the haloalkyl iodide used may be appropriately determined
in the range of molar equivalents of 1 to 10 times the amount of
the compound represented formula (35). The solvent used in this
step is not limited to those described in the above document, and
any solvent which does not significantly inhibit the progress of
reaction can be used as the solvent. Examples of the solvent
include aromatic hydrocarbons such as benzene, toluene, and xylene;
halogenated hydrocarbons such as dichloromethane, chloroform, and
carbon tetrachloride; chained or cyclic ethers such as diethyl
ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters
such as ethyl acetate and butyl acetate; ketones such as acetone,
methyl isobutyl ketone, and cyclohexanone; amides such as
dimethylformamide and dimethylacetamide; nitrites such as
acetonitrile; and inert solvents such as
1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide.
These solvents can be used alone or in a mixture of two ore more
kinds. In particular, a polar solvent is preferred. The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflex temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours.
10-(ii) Formula (37) .fwdarw.Formula (38)
[0122] A compound represented by formula (38) can be produced by
using an appropriate halogenating agent according to the technique
described in, for example, Synth. Commun., p. 1261 (1989). Examples
of the halogenating agent include chlorine, bromine, iodine,
N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. The
amount of the halogenating agent used may be appropriately
determined in the range of molar equivalents of 1 to 10 times the
amount of the compound represented formula (37). The number of
equivalents of the halogenating agent used can be appropriately
determined so that only Y.sub.10 or Y.sub.13 is a halogen atom. In
this step, an appropriate solvent may be used. The solvent used is
not limited to those described in the above document, and any
solvent which does not significantly inhibit the progress of
reaction can be used as the solvent. Examples of the solvent
include aromatic hydrocarbons such as benzene, toluene, and xylene;
halogenated hydrocarbons such as dichloromethane, chloroform, and
carbon tetrachloride; chained or cyclic ethers such as diethyl
ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters
such as ethyl acetate and butyl acetate; ketones such as acetone,
methyl isobutyl ketone, and cyclohexanone; amides such as
dimethylformamide and dimethylacetamide; nitrites such as
acetonitrile; and inert solvents such as
1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide.
These solvents can be used alone or in a mixture of two ore more
kinds. In particular, a polar solvent is preferred. The reaction
temperature may be appropriately determined in the range of
-20.degree. C. to the reflux temperature of the solvent used, and
the reaction time may be appropriately determined in the range of
several minutes to 96 hours.
10-(iii) Formula (38) .fwdarw.Formula (39)
[0123] A compound represented by formula (39) can be produced by
using an appropriate oxidizing agent according to the technique
described in, for example, Tetrahedron Lett., p. 4955 (1994).
Examples of the oxidizing agent include organic peroxy acids such
as m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen
peroxide; ozone; selenium dioxide, chromic acid; dinitrogen
tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide;
iodosylbenzene; and t-butyl hypochlorite. The solvent used in this
step is not limited to those disclosed in the above document, and
any solvent which does not significantly inhibit the progress of
reaction may be used. The solvents can be used alone or in a
mixture of one or more kinds. In particular, a polar solvent is
preferred. The reaction temperature may be appropriately determined
in the range of -20.degree. C. to the reflux temperature of the
solvent used, and the reaction time may be appropriately determined
in the range of several minutes to 96 hours.
10-(iv) Formula (38) .fwdarw.Formula (38-2)
[0124] A compound represented by formula (38-2) (wherein R.sub.7,
Y.sub.11, Y.sub.12, and m each represent the same as described
above, Y.sub.10a and Y.sub.13a each represent a hydrogen atom, a
halogen atom, or a methyl group as far as this step is concerned,
and one of Y.sub.10a and Y.sub.13a necessarily represents a methyl
group) can be produced from the compound represented by formula
(38) using an appropriate methylating agent. This step can be
performed according to the technique described in, for example,
Tetrahedron. Lett., p. 6237 (2000).
10-(v) Formula (38-2) .fwdarw.Formula (39-2)
[0125] A compound represented by formula (39-2) (wherein R.sub.7,
Y.sub.11, Y.sub.12, and m each represent the same as described
above, Y.sub.10a and Y.sub.13a both represent a methyl group or one
of Y.sub.10a and Y.sub.13a represents a methyl group and the other
represents a halogen atom as far as this step is concerned) can be
produced according to the technique descried above in the step
10-(iii) of Production Method 10.
[0126] The compounds represented by formula (1), (3), (4), and (8)
can be produced from aniline derivatives represented by formula
(38), (39), (38-2) and (39-2) according to any one Method
appropriately selected from Production Methods 1 to 9.
[0127] The compound represented by formula (39) can also be
produced from an aminothiophenol represented by formula (40)
according to Production Method 11 (in the formula, R.sub.7,
Y.sub.10, Y.sub.11, Y.sub.12, Y.sub.13, and m each represent the
same as described above). ##STR23##
[0128] Reaction with a haloalkyl iodide and subsequent oxidation
can be performed according to Production Method 10. The compounds
represented by formula (1), (3), (4), and (8) can be produced from
aniline derivatives represented by formula (41) and (42) according
to any one Method appropriately selected from Production Methods 1
to 9.
[0129] A compound represented by formula (9) can also be produced
from an aniline derivative represented by formula (41) and used as
a starting material according to Production Method 12 (in the
formula, R.sub.10, R.sub.11, R.sub.12, Y.sub.14, Y.sub.15,
Y.sub.16, and Y.sub.17 each represent the same as described above).
##STR24##
[0130] A compound represented by formula (9) can be produced by
using an appropriate perfluorinated aldehyde or perfluorinated
ketone according to the technique described in, for example, J. Am.
Chem. Soc., p. 2410 (1965) and J. Org. Chem., p. 1001 (1965).
Examples of the perfluorinated aldehyde or perfluorinated ketone
include hexafluoroacetone and perfluoro-2-butanone. In this step,
an appropriate solvent can be used. The solvent used in this step
is not limited to those disclosed in the above documents, and any
solvent which does not significantly inhibit the progress of
reaction may be used. The solvents can be used alone or in a
mixture of one or more kinds. The reaction temperature may be
appropriately determined in the range of -20.degree. C. to
200.degree. C., and the reaction time may be appropriately
determined in the range of several minutes to 96 hours.
[0131] The compounds represented by formula (1), (3), and (4) can
be produced from an aniline derivative represented by formula (9)
according to any one properly selected from Production Methods 1 to
9.
[0132] In all the production Methods, the compounds may be isolated
from the reaction systems after reactions according to a normal
technique. However, the compounds can be optionally purified by an
operation such as recrystallization, column chromatography,
distillation, or the like. Alternatively, the compounds may be used
in next reaction steps without being isolated from the reaction
systems.
[0133] Although typical examples of the compounds represented by
formula (1) and used as active ingredients of insecticides of the
present invention are shown in Tables 1 to 5, the present invention
is not limited to these examples.
[0134] Although typical examples of the compounds represented by
formula (4) are shown in Tables 6 to 8, the present invention is
not limited to these examples.
[0135] In the tables, "n-" denotes normal, "Me" denotes a methyl
group, "Et" denotes an ethyl group; "n-Pr" denotes a normal propyl
group, "i-Pr, denotes an isopropyl group, "n-Bu" denotes a normal
butyl group, "i-Bu" denotes an isobutyl group, "s-Bu" denotes a
secondary butyl group, "t-Bu" denotes a tertiary butyl group, "H"
denotes a hydrogen atom, "O" denotes an oxygen atom, "S" denotes a
sulfur atom, "C" denotes a carbon atom, "N" denotes a nitrogen
atom, "F" denotes a fluorine atom, "Cl" denotes a chlorine atom,
"Br" denotes a bromine atom, "I" denotes an iodine atom, "CF.sub.3"
denotes a trifluoromethyl group, "MeO" denotes a methoxy group,
"NH.sub.2" denotes an amino group, "MeNH" denotes a methylamino
group, and "Me.sub.2N" denotes a dimethylamino group.
TABLE-US-00001 TABLE 1 (1-A) ##STR25## Compound No. R.sub.1 Q 1 Me
2-methyl-4-heptafluoroisopropylphenyl 2 Et
2-methyl-4-heptafluoroisopropylphenyl 3 i-Pr
2-methyl-4-heptafluoroisopropylphenyl 4 n-Bu
2-methyl-4-heptafluoroisopropylphenyl 5 i-Bu
2-methyl-4-heptafluoroisopropylphenyl 6 s-Bu
2-methyl-4-heptafluoroisopropylphenyl 7 t-Bu
2-methyl-4-heptafluoroisopropylphenyl 8 neopentyl
2-methyl-4-heptafluoroisopropylphenyl 9 3,3-dimethyl-n-butyl
2-methyl-4-heptafluoroisopropylphenyl 10 2-ethyl-n-hexyl
2-methyl-4-heptafluoroisopropylphenyl 11 vinyl
2-methyl-4-heptafluoroisopropylphenyl 12 allyl
2-methyl-4-heptafluoroisopropylphenyl 13
2-isopropyl-5-methylcyclohexyl
2-methyl-4-heptafluoroisopropylphenyl 14 benzyl
2-methyl-4-heptafluoroisopropylphenyl 15 3-cyanobenzyl
2-methyl-4-heptafluoroisopropylphenyl 16 4-cyanobenzyl
2-methyl-4-heptafluoroisopropylphenyl 17 2-methoxyethyl
2-methyl-4-heptafluoroisopropylphenyl 18 chloromethyl
2-methyl-4-heptafluoroisopropylphenyl 19 2-chloroethyl
2-methyl-4-heptafluoroisopropylphenyl 20 2,2,2-trichloroethyl
2-methyl-4-heptafluoroisopropylphenyl 21 1,2,2,2-tetrachloroethyl
2-methyl-4-heptafluoroisopropylphenyl 22
1,1-dimethyl-2,2,2-trichloroethyl
2-methyl-4-heptafluoroisopropylphenyl 23 3-trifluoromethylphenyl
2-methyl-4-heptafluoroisopropylphenyl 24 4-methylphenyl
2-methyl-4-heptafluoroisopropylphenyl 25 4-chlorophenyl
2-methyl-4-heptafluoroisopropylphenyl 26 cyclobutyl
2-methyl-4-heptafluoroisopropylphenyl 27 cyclopentyl
2-methyl-4-heptafluoroisopropylphenyl 28 2-cyanoethyl
2-methyl-4-heptafluoroisopropylphenyl 29 2-(ethylthio)ethyl
2-methyl-4-heptafluoroisopropylphenyl 30 2-(ethylsulfinyl)ethyl
2-methyl-4-heptafluoroisopropylphenyl 31 2-(ethylsulfonyl)ethyl
2-methyl-4-heptafluoroisopropylphenyl 32 2-fluoroethyl
2-methyl-4-heptafluoroisopropylphenyl 33 2,2-difluoroethyl
2-methyl-4-heptafluoroisopropylphenyl 34 2,2,2-trifluoroethyl
2-methyl-4-heptafluoroisopropylphenyl 35 1,3-difluoro-2-propyl
2-methyl-4-heptafluoroisopropylphenyl 36 1-chloro-3-fluoro-2-propyl
2-methyl-4-heptafluoroisopropylphenyl 37 1-methyl-2,2,2-
2-methyl-4-heptafluoroisopropylphenyl trifluoro-2-propyl 38
3,3,3-trifluoro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 39
3,3,4,4,4-pentafluoro-2-butyl 2-methyl-4-heptafluoroisopropylphenyl
40 4,4,4-trifluoro-n-butyl 2-methyl-4-heptafluoroisopropylphenyl 41
2,2,3,3-tetrafluorocyclobutyl 2-methyl-4-heptafluoroisopropylphenyl
42 2,2-dichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 43
1,3-dichloro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl 44
3-chloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 45
3,3,3-trichloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 46
2-bromoethyl 2-methyl-4-heptafluoroisopropylphenyl 47
2,2,2-tribromoethyl 2-methyl-4-heptafluoroisopropylphenyl 48
2-iodoethyl 2-methyl-4-heptafluoroisopropylphenyl 49
tetrahydrofuran-3-yl 2-methyl-4-heptafluoroisopropylphenyl 50
(furan-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 51
(furan-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 52
(tetrahydrofuran-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl
53 (tetrahydrofuran-3-yl)methyl
2-methyl-4-heptafluoroisopropylphenyl 54 (thiophen-2-yl)methyl
2-methyl-4-heptafluoroisopropylphenyl 55 (thiophen-3-yl)methyl
2-methyl-4-heptafluoroisopropylphenyl 56 (pyridin-2-yl)methyl
2-methyl-4-heptafluoroisopropylphenyl 57 (pyridin-3-yl)methyl
2-methyl-4-heptafluoroisopropylphenyl 58
(6-chloropyridin-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl
59 Me 2,6-dimethyl-4-heptafluoroisopropylphenyl 60 Et
2,6-dimethyl-4-heptafluoroisopropylphenyl 61 n-Pr
2,6-dimethyl-4-heptafluoroisopropylphenyl 62 i-Pr
2,6-dimethyl-4-heptafluoroisopropylphenyl 63 n-Bu
2,6-dimethyl-4-heptafluoroisopropylphenyl 64 i-Bu
2,6-dimethyl-4-heptafluoroisopropylphenyl 65 s-Bu
2,6-dimethyl-4-heptafluoroisopropylphenyl 66 t-Bu
2,6-dimethyl-4-heptafluoroisopropylphenyl 67 neopentyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 68 1,2-dimethyl-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 69 1-methyl-n-butyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 70 1,3-dimethyl-n-butyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 71 3,3-dimethyl-n-butyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 72 cyclopentylmethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 73 1-phenylethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 74 2-phenylethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 75 vinyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 76 allyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 77 propargyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 78 cyclobutyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 79 cyclopentyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 80 cyclohexyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 81 benzyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 82 4-methylbenzyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 83
4-tritluoromethylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
84 3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 85
4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 86
2-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 87
3-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 88
4-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 89
2-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 90
3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 91
4-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 92
4-nitrobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 93
4-methoxycarbonylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
94 2-hydroxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 95
2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 96
2-ethoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 97
2-isopropyloxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 98
2-benzyloxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 99
3-ethoxy-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 100
ethoxycarbonylmethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 101
1-(methoxycarbonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
102 1-(ethoxycarbonyl)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 103 3-oxo-n-butyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 104 2-acetoxyethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 105 cyanomethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 106 2-cyanoethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 107 3-cyano-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 108 2-(methylthio)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 109 2-(ethylthio)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 110
2-(isopropylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
111 1-methyl-2-(methylthio)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 112
2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
113 2-(ethylsulfonyl)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 114
3-(methylthio)-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
115 3-(ethylthio)-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 116 2-fluoroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 117 2,2-difluoroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 118 2,2,2-trifluoroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 119 1,3-difluoro-2-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 120
1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 121
1-methyl-2,2,2-trifluoroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 122
1,1,1,3,3,3-hexafluoro-2-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 123
3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
124 2,2,3,3,3-pentafluoro-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 125
3,3,4,4,4-pentafluoro-2-butyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 126
4,4,4-tifluoro-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
127 2,2,3,3-tetrafluorocyclobutyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 128 chloromethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 129 trichloromethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 130 2-chloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 131 2,2-dichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 132 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 133
1,2,2,2-tetrachloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
134 1,3-dichloro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
135 1,1-dimethyl-2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 136 3-chloro-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 137 2-bromoethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 138 2,2,2-tribromoethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 139 3-bromo-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 140 2-iodoethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 141 2-(acetylamino)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 142
2-(dimethylamino)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
143 2-(ethylamino)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
144 methylaminocarbonylethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 145 phenyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 146 4-methylphenyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 147
3-trifluoromethylphenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
148 4-chlorophenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 149
naphthyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 150
Pyridine-2-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 151
pyridine-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 152
pyridine-4-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 153
tetrahydrofuran-2-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 154
tetrahydrofuran-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 155
(furan-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 156
(furan-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 157
(tetrahydrofuran-2-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 158
(tetrahydrofuran-3-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 159 (thiophen-2-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 160 (thiophen-3-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 161 (pyridin-2-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 162 (pyridin-3-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 163
(6-chloropyridin-3-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 164 Me
2-methyl-6-isopropyl-4-heptafluoro isopropylphenyl 165 Et
2-methyl-6-isopropyl-4-heptafluoro isopropylphenyl 166 i-Pr
4-heptafluoroisopropylphenyl 167 i-Pr
3-methyl-4-heptafluoroisopropylphenyl 168 i-Pr
2-ethyl-4-heptafluoroisopropylphenyl 169 i-Pr
2-propyl-4-heptafluoroisopropylphenyl 170 i-Pr
3-methoxy-4-heptafluoroisopropylphenyl 171 i-Pr
3-chloro-4-heptafluoroisopropylphenyl 172 i-Pr
2,3-dimethyl-4-heptafluoroisopropylphenyl 173 i-Pr
2,5-dimethyl-4-heptafluoroisopropylphenyl 174 i-Pr
2,6-diethyl-4-heptafluoroisopropylphenyl 175 i-Pr
2-ethyl-6-methyl-4-heptafluoroisopropylphenyl 176 i-Pr
2-methyl-6-isopropyl-4-heptafluoroisopropyl phenyl 177 i-Pr
2-methoxy-6-methyl-4-heptafluoroisopropylphenyl 178 i-Pr
2-methyl-6-phenyl4-heptafluoroisopropylphenyl 179 i-Pr
2-chloro-5-methyl-4-heptafluoroisopropylphenyl 180 i-Pr
2-chloro-6-ethyl-4-heptafluoroisopropylphenyl 181 i-Pr
2-chloro-6-n-propyl-4-heptafluoroisopropyl phenyl 182 i-Pr
2-chloro-5-methoxy-4-heptafluoroisopropylphenyl 183 i-Pr
2,3-dimethyl-6-chloro-4-heptafluoroisopropyl phenyl 184 i-Pr
2-chloro-3,6-dimethyl-4-heptafluoroisopropyl phenyl 185 i-Pr
2-methyl-3-chloromethyl-6-chloro-4-heptafluoro isopropylphenyl 186
i-Pr 2-methyl-3-iodo-6-chloro-4-heptafluoro isopropylphenyl 187
2,2,2-trichloroethyl 4-heptafluoroisopropylphenyl 188
2,2,2-trichloroethyl 3-methyl-4-heptafluoroisopropylphenyl 189
2,2,2-trichloroethyl 2-ethyl-4-heptafluoroisopropylphenyl 190
2,2,2-trichloroethyl 2-propyl-4-heptafluoroisopropylphenyl 191
2,2,2-trichloroethyl 3-methoxy-4-heptafluoroisopropylphenyl 192
2,2,2-trichloroethyl 2-chloro-4-heptafluoroisopropylphenyl 193
2,2,2-trichloroethyl 3-chloro-4-heptafluoroisopropylphenyl 194
2,2,2-trichloroethyl 2,3-dimethyl-4-heptafluoroisopropylphenyl 195
2,2,2-trichloroethyl 2,5-dimethyl-4-heptafluoroisopropylphenyl 196
2,2,2-trichloroethyl 2,6-diethyl-4-heptafluoroisopropylphenyl 197
2,2,2-trichloroethyl 2-ethyl-6-methyl-4-heptafluoroisopropylphenyl
198 2,2,2-trichloroethyl 2-methyl-6-isopropyl-4-heptafluoro
isopropylphenyl 199 2,2,2-trichloroethyl
2-methoxy-6-methyl-4-heptafluoroisopropylphenyl 200
2,2,2-trichloroethyl 2-methyl-6-phenyl-4-heptafluoroisopropylphenyl
201 2,2,2-trichloroethyl 2-hydroxy-6-methyl-4-heptafluoroisopropyl
phenyl 202 2,2,2-trichloroethyl
2-chloro-5-methyl-4-heptafluoroisopropylphenyl 203
2,2,2-trichloroethyl 2-methyl-3-amino-4-heptafluoroisopropylphenyl
204 2,2,2-trichloroethyl
2-methyl-3-t-butoxycarbonylamino-4-heptafluoro isopropylphenyl 205
2,2,2-trichloroethyl 2-chloro-6-ethyl-4-heptafluoroisopropylphenyl
206 2,2,2-trichloroethyl
2-bromo-6-ethyl-4-heptafluoroisopropylphenyl 207
2,2,2-trichloroethyl 2-ethyl-6-iodo-4-heptafluoroisopropylphenyl
208 2,2,2-trichloroethyl 2-chloro-6-n-propyl-4-heptafluoro
isopropylphenyl 209 2,2,2-trichloroethyl
2-bromo-6-n-propyl-4-heptafluoro isopropylphenyl 210
2,2,2-trichloroethyl 2-bromo-6-n-butyl-4-heptafluoro
isopropylphenyl 211 2,2,2-trichloroethyl
2-chloro-5-methoxy-4-heptafluoro isopropylphenyl 212
2,2,2-trichloroethyl 2-bromo-6-methylthio-4-heptafluoro
isopropylphenyl 213 2,2,2-trichloroethyl
2,6-dichloro-4-heptafluoroisopropylphenyl
214 2,2,2-trichloroethyl 2,3-dimethyl-6-chloro-4-heptafluoro
isopropylphenyl 215 2,2,2-trichloroethyl
2-chloro-3,6-dimethyl-4-heptafluoro isopropylphenyl 216
2,2,2-trichloroethyl 2-methyl-3-chloromethyl-6-chloro-4-heptafluoro
isopropylphenyl 217 2,2,2-trichloroethyl
2-methyl-3,6-dichloro-4-heptafluoro isopropylphenyl 218
2,2,2-trichloroethyl 2-methyl-3-bromo-6-chloro-4-heptafluoro
isopropylphenyl 219 2,2,2-trichloroethyl
2-methyl-3-iodo-6-chloro-4-heptafluoro isopropylphenyl 220
2,2,2-trichloroethyl 2-methyl-3-amino-6-chloro-4-heptafluoro
isopropylphenyl 221 3,3,3-trifluoro-n-propyl
2-bromo-6-n-butyl-4-heptafluoro isopropylphenyl 222 i-Pr
2-chloro-6-methyl-4-trifluoromethylphenyl 223 i-Pr
2,6-dichloro-4-trifluoromethylphenyl 224 i-Pr
2-bromo-4,6-bis(trifluoromethyl)phenyl 225 i-Pr
2,6-dimethyl-4-heptafluoro-n-propylphenyl 226 i-Pr
2,6-dimethyl-4-nonafluoro-n-butylphenyl 227 2,2,2-trichloroethyl
4-trifluoromethylphenyl 228 2,2,2-trichloroethyl
2-chloro-6-methyl-4-trifluoromethylphenyl 229 2,2,2-trichloroethyl
2-bromo-6-chloro-4-trifluoromethylphenyl 230 2,2,2-trichloroethyl
2,6-dichloro-4-trifluoromethylphenyl 231 2,2,2-trichloroethyl
2-chloro4,6-bistrifluoromethylphenyl 232 2,2,2-trichloroethyl
2-bromo-4,6-bistrifluoromethylphenyl 233 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoro-n-propylphenyl 234 2,2,2-trichloroethyl
2,6-dimethyl-4-nonafluoro-n-butylphenyl 235 2,2,2-trichloroethyl
2,3,5,6-tetrafluoro-4-trifluoromethylphenyl 236
2,2,2-trichloroethyl 2,6-dibromo-4-pentafluoroethylphenyl 237
3,3,3-trifluoro-n-propyl 2,6-dibromo-4-pentafluoroethylphenyl 238
3,3,3-trifluoro-n-propyl 2-bromo6-chloro-4-trifluoromethylphenyl
239 Et 2,4-bis(trifluoromethyl)phenyl 240 i-Pr
2,4-bis(trifluoromethyl)phenyl 241 vinyl
2,4-bis(trifluoromethyl)phenyl 242 cyclopentyl
2,4-bis(trifluoromethyl)phenyl 243 2-chloroethyl
2,4-bis(trifluoromethyl)phenyl 244 2-cyanoethyl
2,4-bis(trifluoromethyl)phenyl 245 2,2-difluoroethyl
2,4-bis(trifluoromethyl)phenyl 246 2,2-dichloroethyl
2,4-bis(trifluoromethyl)phenyl 247 2,2,2-trichloroethyl
2,4-bis(trifluoromethyl)phenyl 248 2,2,2-tribromoethyl
2,4-bis(trifluoromethyl)phenyl 249 3,3,3-trifluoro-n-propyl
2,4-bis(trifluoromethyl)phenyl 250 2,2,3,3,3-pentafluoro-n-propyl
2,4-bis(trifluoromethyl)phenyl 251 4-cyanobenzyl
2,4-bis(trifluoromethyl)phenyl 252 (6-chloropyridin-3-yl)methyl
2,4-bis(trifluoromethyl)phenyl 253 i-Pr
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 254 2,2-difluoroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 255 1,3-difluoro-2-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 256 2,2,2-trifluoroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 257 2,2,2-trichloroethyl
2,6-dimethyl-4-(noanfluoro-2-butyl)phenyl 258
1-methyl-2,2,2-trifluoroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 259
3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
260 Et 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 261 vinyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 262 propargyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 263 cyclobutyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 264 cyclopentyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 265 benzyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 266 3-cyanobenzyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 267 4-cyanobenzyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 268 3-chlorobenzyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 269 2-methoxyethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 270 2-cyanoethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 271 2-(methylthio)ethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 272 2-(ethylthio)ethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 273
1-methyl-2-(methylthio)ethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 274
2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
275 2-(ethylsulfonyl)ethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 276 2-fluoroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 277
1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 278
2,2,3,3,3-pentafluoro-n-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 279
3,3,4,4,4-pentafluoro-2-butyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 280
4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
281 2,2,3,3-tetrafluorocyclobutyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 282 2-chloroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 283 2,2-dichloroethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 284 1,3-dichloro-2-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 285 3-chloro-n-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 286 2-bromoethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 287 2,2,2-tribromoethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 288 3-bromo-n-propyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 289 2-iodoethyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 290 tetrahydrofuran-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 291 (furan-2-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 292 (furan-3-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 293
(tetrahydrofuran-2-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 294
(tetrahydrofuran-3-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 295 (thiophen-2-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 296 (thiophen-3-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 297 (pyridin-2-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 298 (pyridin-3-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 299
(6-chloropyridin-3-yl)methyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 300 2,2,2-trichloroethyl
2,6-dichloro-4-(trifluoromethylthio)phenyl 301 2,2,2-trichloroethyl
2,6-dichloro-4-(trifluoromethylsulfonyl)phenyl 302 Et
2,6-dimethyl-4-pentafluoroethylphenyl 303 i-Pr
2,6-dimethyl-4-pentafluoroethylphenyl 304 propargyl
2,6-dimethyl-4-pentafluoroethylphenyl 305 cyclobutyl
2,6-dimethyl-4-pentafluoroethylphenyl 306 cyclopentyl
2,6-dimethyl-4-pentafluoroethylphenyl 307 benzyl
2,6-dimethyl-4-pentafluoroethylphenyl 308 3-cyanobenzyl
2,6-dimethyl-4-pentafluoroethylphenyl 309 4-cyanobenzyl
2,6-dimethyl-4-pentafluoroethylphenyl 310 3-chlorobenzyl
2,6-dimethyl-4-pentafluoroethylphenyl 311 2-methoxyethyl
2,6-dimethyl-4-pentafluoroethylphenyl 312 2-cyanoethyl
2,6-dimethyl-4-pentafluoroethylphenyl 313 2-(methylthio)ethyl
2,6-dimethyl-4-pentafluoroethylphenyl 314 2-(ethylthio)ethyl
2,6-dimethyl-4-pentafluoroethylphenyl 315
1-methyl2-(methylthio)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl
316 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl
317 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl
318 2-fluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 319
2,2-difluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 320
2,2,2-trifluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 321
1,3-difluoro-2-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 322
1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-pentafluoroethylphenyl
323 1-methyl-2,2,2-trifluoroethyl
2,6-dimethyl-4-pentafluoroethylphenyl 324 3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-pentafluoroethylphenyl 325
2,2,3,3,3-pentafluoro-n-propyl
2,6-dimethyl-4-pentafluoroethylphenyl 326
3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-pentafluoroethylphenyl
327 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-pentafluoroethylphenyl
328 2,2,3,3-tetrafluorocyclobutyl
2,6-dimethyl-4-pentafluoroethylphenyl 329 2-chloroethyl
2,6-dimethyl-4-pentafluoroethylphenyl 330 2,2-dichloroethyl
2,6-dimethyl-4-pentafluoroethylphenyl 331 2,2,2-trichloroethyl
2,6-dimethyl-4-pentafluoroethylphenyl 332 1,3-dichloro-2-propyl
2,6-dimethyl-4-pentafluoroethylphenyl 333 3-chloro-n-propyl
2,6-dimethyl-4-pentafluoroethylphenyl 334 2-bromoethyl
2,6-dimethyl-4-pentafluoroethylphenyl 335 2,2,2-tribromoethyl
2,6-dimethyl-4-pentafluoroethylphenyl 336 3-bromo-n-propyl
2,6-dimethyl-4-pentafluoroethylphenyl 337 2-iodoethyl
2,6-dimethyl-4-pentafluoroethylphenyl 338 tetrahydrofuran-3-yl
2,6-dimethyl-4-pentafluoroethylphenyl 339 (furan-2-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 340 (furan-3-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 341
(tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl
342 (tetrahydrofuran-3-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 343 (thiophen-2-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 344 (thiophen-3-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 345 (pyridin-2-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 346 (pyridin-3-yl)methyl
2,6-dimethyl-4-pentafluoroethylphenyl 347
(6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl
348 Me 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 349 Et
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl
350 i-Pr 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 351 propargyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
352 cyclobutyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 353 cyclopentyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl
354 3-cyanobenzyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 355 4-cyanobenzyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl
356 3-chlorobenzyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 357 2-methoxyethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl
358 2-cyanoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 359 2-(methylthio)ethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl
360 2-(ethylthio)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-
hexafluoro-isopropyl)phenyl 361 1-methyl-2-(methylthio)ethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
362 2-(ethylsulfinyl)ethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
363 2-(ethylsulfonyl)ethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
364 2-fluoroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 365 2,2-difluoroethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
366 2,2,2-trifluoroethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
367 1,3-difluoro-2-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
368 1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
369 1-methyl-2,2,2-trifluoroethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
370 3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
371 2,2,3,3,3-pentafluoro-n-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
372 3,3,4,4,4-pentafluoro-2-butyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 373
4,4,4-trifluoro-n-butyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 374
2,2,3,3-tetrafluorocyclobutyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
375 2-chloroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 376 2,2-dichloroethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
377 2,2,2-trichloroethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
378 1,3-dichloro-2-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
379 3-chloro-n-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
380 2-bromoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 381 2,2,2-tribromoethyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
382 3-bromo-n-propyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
383 2-iodoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 384 tetrahydrofuran-3-yl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
385 (furan-2-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
386 (furan-3-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
387 (tetrahydrofuran-2-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
388 (tetrahydrofuran-3-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
389 (thiophen-2-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
390 (thiophen-3-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 391
(pyridin-2-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
392 (pyridin-3-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro-
isopropyl)phenyl 393 (6-chloropyridin-3-yl)methyl
2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl
394 Et 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 395 i-Pr
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 396 vinyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 397 propargyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 398 cyclobutyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 399 cyclopentyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 400 benzyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 401 3-cyanobenzyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 402 4-cyanobenzyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 403 3-chlorobenzyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 404 2-methoxyethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 405 2-cyanoethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 406
2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
407 2-(ethylthio)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 408
1-methyl-2-(methylthio)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 409
2-(ethylsulfinyl)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 410
2-(ethylsulfonyl)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 411 2-fluoroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 412
2,2-difluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
413 2,2,2-trifluoroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 414
1,3-difluoro-2-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 415
1-chloro-3-fluoro-2-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 416
1-methyl-2,2,2-trifluoroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 417
3,3,3-trifluoro-n-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 418
2,2,3,3,3-pentafluoro-n-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 419
3,3,4,4,4-pentafluoro-2-butyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 420
4,4,4-trifluoro-n-butyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 421
2,2,3,3-tetrafluorocyclobutyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 422 2-chloroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 423
2,2-dichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
424 2,2,2-trichloroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 425
1,3-dichloro-2-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 426
3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
427 2-bromoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
428 2,2,2-tribromoethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 429
3-bromo-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
430 2-iodoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 431
tetrahydrofuran-3-yl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 432
(furan-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
433 (furan-3-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 434
(tetrahydrofuran-2-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 435
(tetrahydrofuran-3-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 436
(thiophen-2-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 437
(thiophen-3-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 438
(pyridin-2-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 439
(pyridin-3-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 440
(6-chloropyridin-3-yl)methyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 441 Et
2,6-dibromo-4-(trifluoromethylthio)phenyl 442 i-Pr
2,6-dibromo-4-(trifluoromethylthio)phenyl 443 vinyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 444 propargyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 445 cyclobutyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 446 cyclopentyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 447 benzyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 448 3-cyanobenzyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 449 4-cyanobenzyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 450 3-chlorobenzyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 451 2-methoxyethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 452 2-cyanoethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 453 2-(methylthio)ethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 454 2-(ethylthio)ethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 455
1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 456
2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
457 2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 458 2-fluoroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 459 2,2-difluoroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 460 2,2,2-trifluoroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 461 1,3-difluoro-2-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 462
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 463
1-methyl-2,2,2-trifluoroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 464
3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
465 2,2,3,3,3-pentafluoro-n-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 466
3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 467
4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
468 2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 469 2-chloroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 470 2,2-dichloroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 471 2,2,2-trichloroethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 472 1,3-dichloro-2-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 473 3-chloro-n-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 474 2-bromoethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 475 2,2,2-tribromoethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 476 3-bromo-n-propyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 477 2-iodoethyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 478 tetrahydrofuran-3-yl
2,6-dibromo-4-(trifluoromethylthio)phenyl 479 (furan-2-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 480 (furan-3-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 481
(tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 482
(tetrahydrofuran-3-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 483 (thiophen-2-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 484 (thiophen-3-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 485 (pyridin-2-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 486 (pyridin-3-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 487
(6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(trifluoromethylthio)phenyl 488 Et
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 489 i-Pr
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 490 vinyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 491 propargyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 492 cyclobutyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 493 cyclopentyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 494 benzyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 495 3-cyanobenzyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 496 4-cyanobenzyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 497 3-chlorobenzyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 498 2-methoxyethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 499 2-cyanoethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 500
2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
501 2-(ethylthio)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 502
1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 503
2-(ethylsulfinyl)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 504
2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 505 2-fluoroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 506 2,2-difluoroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 507
2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
508 1,3-difluoro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 509
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 510
1-methyl-2,2,2-trifluoroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 511
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 512
2,2,3,3,3-pentafluoro-n-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 513
3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 514
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 515
2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 516 2-chloroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 517 2,2-dichloroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 518
2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
519 1,3-dichloro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 520 3-chloro-n-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 521 2-bromoethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 522
2,2,2-tribromoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
523 3-bromo-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
524 2-iodoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 525
tetrahydrofuran-3-yl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
526 (furan-2-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 527
(furan-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
528 (tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 529
(tetrahydrofuran-3-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 530
(thiophen-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
531 (thiophen-3-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 532
(pyridin-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
533 (pyridin-3-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 534
(6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 535 Et
2,6-dibromo-4-(pentafluoroethylthio)phenyl 536 i-Pr
2,6-dibromo-4-(pentafluoroethylthio)phenyl 537 vinyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 538 propargyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 539 cyclobutyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 540 cyclopentyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 541 benzyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 542 3-cyanobenzyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 543 4-cyanobenzyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 544 3-chlorobenzyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 545 2-methoxyethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 546 2-cyanoethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 547 2-(methylthio)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 548 2-(ethylthio)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 549
1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 550
2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
551 2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 552 2-fluoroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 553 2,2-difluoroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 554 2,2,2-trifluoroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 555
1,3-difluoro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
556 1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 557
1-methyl-2,2,2-trifluoroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 558
3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
559 2,2,3,3,3-pentafluoro-n-propyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 560
3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 561
4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
562 2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 563 2-chloroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 564 2,2-dichloroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 565 2,2,2-trichloroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 566
1,3-dichloro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
567 3-chloro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
568 2-bromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 569
2,2,2-tribromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 570
3-bromo-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 571
2-iodoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 572
tetrahydrofuran-3-yl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 573
(furan-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 574
(furan-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 575
(tetrehydrofuran-2-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 576
(tetrahydrofuran-3-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 577
(thiophen-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
578 (thiophen-3-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 579 (pyridin-2-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 580 (pyridin-3-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 581
(6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 582 Et
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 583 i-Pr
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 584 vinyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 585 propargyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 586 cyclobutyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 587 cyclopentyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 588 benzyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 589 3-cyanobenzyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 590 4-cyanobenzyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 591 3-chlorobenzyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 592 2-methoxyethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 593 2-cyanoethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 594
2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
595 2-(ethylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 596
1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 597
2-(ethylsulfinyl)ethyl
2,8-dibromo-4-(heptafluoro-n-propylthio)phenyl 598
2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 599 2-fluoroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 600
2,2-difluoroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
601 2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 602
1,3-difluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 603
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 604
1-methyl-2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 605
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 606
2,2,3,3,3-pentafluoro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 607
3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 608
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 609
2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 610 2-chloroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 611
2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
612 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 613
1,3-dichloro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 614
3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
615 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 616
2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
617 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
618 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 619
tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
620 (furan-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 621
(furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
622 (tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 623
(tetrahydrofuran-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 624
(thiophen-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 625
(thiophen-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 626
(pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
627 (pyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 628
(6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 629 Et
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 630 i-Pr
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 631 vinyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 632 propargyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 633 cyclobutyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 634 cyclopentyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 635 benzyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 636 3-cyanobenzyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 637 4-cyanobenzyl
2,6-dlbromo-4-(heptafluoroisopropylthio)phenyl 638 3-chlorobenzyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 639 2-methoxyethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 640 2-cyanoethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 641
2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
642 2-(ethylthio)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 643
1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 644
2-(ethylsulfinyl)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 645
2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 646 2-fluoroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 647
2,2-difluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
648 2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 649
1,3-difluoro-2-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 650
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 651
1-methyl-2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 652
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 653
2,2,3,3,3-pentafluoro-n-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 654
3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 655
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 656
2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 657 2-chloroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 658
2,2-dichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
659 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 660
1,3-dichloro-2-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 661
3-chloro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
662 2-bromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 663
2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
664 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
665 2-iodoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 666
tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
667 (furan-2-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 668
(furan-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
669 (tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 670
(tetrehydrofuran-3-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 671
(thiophen-2-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 672
(thiophen-3-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 673
(pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
674 (pyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 675
(6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 676 Et
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 677 i-Pr
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 678 vinyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 679 propargyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 680 cyclobutyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 681 cyclopentyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 682 benzyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 683
3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl
684 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 685 3-chlorobenzyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 686
2-methoxyethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl
687 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 688 2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 689
2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 690 1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 691
2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 692 2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 693
2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl
694 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 695 2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 696
1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 697 1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 698
1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 699 3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 700
2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 701 3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 702
4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 703 2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 704
2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl
705 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 706 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 707
1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 708 3-chloro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 709
2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl
710 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 711 3-bromo-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 712 2-iodoethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 713
tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 714 (furan-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 715
(furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 716 (tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 717
(tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 718 (thiophen-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 719
(thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 720 (pyridin-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 721
(pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 722 (6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 723 Et
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 724 i-Pr
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 725 vinyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 726 propargyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 727 cyclobutyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 728 cyclopentyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 729 benzyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 730
3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl
731 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 732 3-chlorobenzyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 733
2-methoxyethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl
734 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 735 2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 736
2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 737 1-methyl-2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 738
2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 739 2-(ethylsulfonyl)ethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 740
2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl
741 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 742 2,2,2-trifluoroethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 743
1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl
phenyl 744 1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 745
1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 746 3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 747
2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 748 3,3,4,4,4-pentafluoro-2-butyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 749
4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 750 2,2,3,3-tetrafluorocyclobutyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 751
2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl
752 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 753 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 754
1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 755 3-chloro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 756
2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl
757 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 758 3-bromo-n-propyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 759 2-iodoethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 760
tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 761 (furan-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 762
(furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 763 (tetrahydrofuran-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 764
(tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 765 (thiophen-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 766
(thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 767 (pyridin-2-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 768
(pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl)phenyl 769 (6-chloropyridin-3-yl)methyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 770
2,2,2-trichloroethyl 2-methyl-4-(heptafluoro-n-propylthio)phenyl
771 Et 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 772 i-Pr
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 773 propargyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 774 cyclobutyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 775 cyclopentyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 776 benzyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
777 3-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
778 4-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
779 3-chlorobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
780 2-methoxyethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
781 2-cyanoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
782 2-(methylthio)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 783
2-(ethylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
784 1-methyl-2-(methylthio)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 785
2-(ethylsulfinyl)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 786
2-(ethylsulfonyl)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 787 2-fluoroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 788
2,2-difluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
789 2,2,2-trifluoroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 790
1,3-difluoro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 791
1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 792
1-methyl-2,2,2-trifluoroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 793
3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 794
2,2,3,3,3-pentafluoro-n-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 795
3,3,4,4,4-pentafluoro-2-butyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 796
4,4,4-trifluoro-n-butyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 797
2,2,3,3-tetrafluorocyclobutyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 798 2-chloroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 799
2,2-dichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
800 2,2,2-trichloroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 801
1,3-dichloro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 802
3-chloro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
803 2-bromoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
804 2,2,2-tribromoethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 805
3-bromo-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
806 2-iodoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 807
tetrahydrofuran-3-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 808
(furan-2-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
809 (furan-3-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 810
(tetrahydrofuran-2-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 811
(tetrahydrofuran-3-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 812
(thiophen-2-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 813
(thiophen-3-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 814
(pyridin-2-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 815
(pyridin-3-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 816
(6-chloropyridin-3-yl)methyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 817
3,3,3-trifluoro-n-propyl
2-(n-butyl)-6-chloro-4-heptafluoroisopropylphenyl 818
3,3,3-trifluoro-n-propyl
2-(n-butyl)-4-heptafluoroisopropyl-6-iodophenyl 819
3,3,3-trifluoro-n-propyl
2-bromo-6-(2-butyl)-4-heptafluoroisopropylphenyl 820 i-Pr
2-methyl-4-trifluoromethoxyphenyl 821 i-Pr
2-trifluoromethyl-4-isopropylphenyl 822 i-Pr
3,5-bistrifluoromethylphenyl 823 i-Pr 2,3,4-trifluorophenyl 824
i-Pr 2-heptafluoroisopropyl-3,5-dimethylphenyl 825 i-Pr
2,4-dichloro-6-methylphenyl 826 i-Pr 2-chloro-4,6-dimethylphenyl
827 i-Pr 2,6-dimethyl-4-chlorophenyl 828 i-Pr
2,6-dimethyl-4-bromophenyl 829 i-Pr 2,6-dimethyl-4-iodophenyl 830
i-Pr 2,6-dimethyl-4-(phenyl)phenyl 831 i-Pr
2,6-dimethyl-4-(2-methylphenyl)phenyl 832 i-Pr
2,6-dimethyl-4-(3-methylphenyl)phenyl 833 i-Pr
2,6-dimethyl-4-(4-methylphenyl)phenyl 834 i-Pr
2,6-dimethyl-4-(2-methoxyphenyl)phenyl 835 i-Pr
2,6-dimethyl-4-(3-methoxyphenyl)phenyl 836 i-Pr
2,6-dimethyl-4-(4-methoxyphenyl)phenyl 837 i-Pr
2,6-dimethyl-4-(4-ethoxyphenyl)phenyl 838 i-Pr
2,6-dimethyl-4-(4-methylthiophenyl)phenyl 839 i-Pr
2,6-dimethyl-4-(2-fluorophenyl)phenyl 840 i-Pr
2,6-dimethyl-4-(3-fluorophenyl)phenyl 841 i-Pr
2,6-dimethyl-4-(4-fluorophenyl)phenyl 842 i-Pr
2-bromo-4-isopropyl-6-methylphenyl 843 i-Pr
2-chloro-4-cyano-6-methylphenyl 844 i-Pr
2-chloro-4-trifluoromethoxy-6-methylphenyl 845 i-Pr
2-chloro-4-isopropyl-6-trifluoromethylphenyl 846 i-Pr
pentafluorophenyl 847 2,2,2-trichloroethyl 4-cyclohexylphenyl 848
2,2,2-trichloroethyl 2-trifluoromethylphenyl 849
2,2,2-trichloroethyl 4-(trifluoromethylthio)phenyl 850
2,2,2-trichloroethyl 4-(trifluoromethylsulfonyl)phenyl 851
2,2,2-trichloroethyl 4-(heptafluoro-n-propylthio)phenyl 852
2,2,2-trichloroethyl 4-(heptafluoro-n-propylsulfinyl)phenyl 853
2,2,2-trichloroethyl 4-(heptafluoroisopropylthio)phenyl 854
2,2,2-trichloroethyl
2-(n-butyl)-6-chloro-4-heptafluoroisopropylphenyl 855
2,2,2-trichloroethyl
2-(n-butyl)-4-heptafluoroisopropyl-6-iodophenyl 856
2,2,2-trichloroethyl
2-bromo-6-(2-butyl)-4-heptafluoroisopropylphenyl 857
2,2,2-trichloroethyl 2-(2-butyl)-4-heptafluoroisopropylphenyl 858
2,2,2-trichloroethyl 2-methyl-4-trifluoromethoxyphenyl 859
2,2,2-trichloroethyl 2-methyl-4-(2,2,2-trifluoroethoxy)phenyl 860
2,2,2-trichloroethyl 2-methyl-4-(trifluoromethylsulfonyloxy)phenyl
861 2,2,2-trichloroethyl 2-methyl-4-chlorophenyl 862
2,2,2-trichloroethyl 2-trifluoromethyl-4-isopropylphenyl 863
2,2,2-trichloroethyl 2,5-bistrifluoromethylphenyl 864
2,2,2-trichloroethyl 3,5-bistrifluoromethylphenyl 865
2,2,2-trichloroethyl 2-trifluoromethyl-4-chlorophenyl 866
2,2,2-trichloroethyl 2-chloro-6-trifluoromethylphenyl 867
2,2,2-trichloroethyl 2-trifluoromethyl-4-iodophenyl 868
2,2,2-trichloroethyl 2-trifluoromethoxy-4-bromophenyl 869
2,2,2-trichloroethyl 2,3,4-trifluorophenyl 870 2,2,2-trichloroethyl
2-heptafluoroisopropyl-3,5-dimethylphenyl 871 2,2,2-trichloroethyl
2,5-dimethyl-4-trifluoromethane sulfonyloxyphenyl 872
2,2,2-trichloroethyl 2,6-dimethyl-4-(bis(trifluoromethyl)
hydroxymethyl)phenyl 873 2,2,2-trichloroethyl
2,6-dimethyl-4-(bis(chlorodifluoromethyl) hydroxymethyl)phenyl 874
2,2,2-trichloroethyl 2,6-dimethyl-4-cyanothiophenyl 875
2,2,2-trichloroethyl 2,6-dimethyl-4-chlorophenyl 876
2,2,2-trichloroethyl 2-chloro-4,6-dimethylphenyl 877
2,2,2-trichloroethyl 2,6-dimethyl-4-bromophenyl 878
2,2,2-trichloroethyl 2,6-dimethyl-4-iodophenyl 879
2,2,2-trichloroethyl 2,6-dimethyl-4-(phenyl)phenyl 880
2,2,2-trichloroethyl 2,6-dimethyl-4-(2-methylphenyl)phenyl 881
2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methylphenyl)phenyl 882
2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methylphenyl)phenyl 883
2,2,2-trichloroethyl 2,6-dimethyl-4-(2-methoxyphenyl)phenyl 884
2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methoxyphenyl)phenyl 885
2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methoxyphenyl)phenyl 886
2,2,2-trichloroethyl 2,6-dimethyl-4-(4-ethoxyphenyl)phenyl 887
2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methylthiophenyl)phenyl 888
2,2,2-trichloroethyl 2,6-dimethyl-4-(2-fluorophenyl)phenyl 889
2,2,2-trichloroethyl 2,6-dimethyl-4-(3-fluorophenyl)phenyl 890
2,2,2-trichloroethyl 2,6-dimethyl-4-(4-fluorophenyl)phenyl 891
2,2,2-trichloroethyl 2,6-dimethyl-4-(3,4-difluorophenyl)phenyl 892
2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methyl-4-fluorophenyl)phenyl
893 2,2,2-trichloroethyl 2,6-dimethyl-4-(furan-3-yl)phenyl 894
2,2,2-trichloroethyl 2,6-dimethyl-4-(thiophene-2-yl)phenyl 895
2,2,2-trichloroethyl 2,6-dimethyl-4-(thiophene-3-yl)phenyl 896
2,2,2-trichloroethyl 2,4-dichloro-6-methylphenyl 897
2,2,2-trichloroethyl 2,4-dichloro-6-trifluoromethylphenyl 898
2,2,2-trichloroethyl
2,6-dichloro-4-(heptafluoroisopropylthio)phenyl 899
2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoroisopropyl
sulfonyl)phenyl 900 2,2,2-trichloroethyl
2,6-dichloro-4-pentafluorosulfanylphenyl 901 2,2,2-trichloroethyl
2,6-dibromo-4-cyclohexylphenyl 902 2,2,2-trichloroethyl
2,4-dibromo-6-trifluoromethylphenyl 903 2,2,2-trichloroethyl
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 904
2,2,2-trichloroethyl 2-chloro-4-hydroxy-6-methylphenyl 905
2,2,2-trichloroethyl 2-chloro-4-trifluoromethoxy-6-methylphenyl 906
2,2,2-trichloroethyl
2-chloro-4-((2,2,2-trichloroethoxy)carbonyloxy)- 6-methylphenyl 907
2,2,2-trichloroethyl 2-chloro-4-cyano-6-methylphenyl 908
2,2,2-trichloroethyl 2-chloro-4-iodo-6-methylphenyl 909
2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-methylphenyl 910
2,2,2-trichloroethyl 2-bromo-4-hydroxy-6-methylphenyl 911
2,2,2-trichloroethyl 2-chloro-4-isopropyl-6-trifluoromethylphenyl
912 2,2,2-trichloroethyl
2-bromo-4-((2,2,2-trichloroethoxy)carbonyloxy)- 6-methylphenyl 913
2,2,2-trichloroethyl 2-chloro-4-bromo-6-trifluoromethylphenyl 914
2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-trifluoromethylphenyl
915 2,2,2-trichloroethyl 2-bromo-4-chloro-6-trifluoromethylphenyl
916 2,2,2-trichloroethyl pentafluorophenyl 917 2-chloroethyl
2,6-dimethyl-4-iodophenyl 918 3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro2- hydroxy-2-propyl)phenyl
919 3,3,3-trifluoro-n-propyl
2,6-dichloro-4-pentafluorosulfanylphenyl 920 i-Pr
2-methyl-4-heptafluoroisopropyl-1-naphthyl 921 i-Pr
4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 922 i-Pr
2-chloro-4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 923
i-Pr 1-methyl-3-trifluoromethylpyrazol-5-yl 924 i-Pr
1-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl 925 i-Pr
1-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl 926 i-Pr
1-methyl-3-trifluoromethyl-4-methoxy carbonylpyrazol-5-yl 927 i-Pr
2-chloro-4-methylpyridin-5-yl 928 i-Pr
2-bromo4-methyl-6-chloropyridin-3-yl 929 i-Pr
2-(1,1,1,3,3,3-hexafluoroisopropyloxy) pyridin-5-yl 930 i-Pr
2-(1,1,1,3,3,3-hexafluoroisopropyloxy)- 4-methylpyridin-5-yl 931
i-Pr 2-bromo-6-(1,1,1,3,3,3-hexafluoro- isopropyloxy)pyridin-3-yl
932 i-Pr 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro-
isopropyloxy)pyridin-3-yl 933 2,2,2-trichloroethyl
2-methyl-4-heptafluoroisopropyl-1-naphthyl 934 2,2,2-trichloroethyl
4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 935
2,2,2-trichloroethyl 2-chloro-4-heptafluoroisopropyl
5,6,7,8-tetrahydro-1-naphthyl 936 2,2,2-trichloroethyl
1-methyl-3-trifluoromethylpyrazol-5-yl 937 2,2,2-trichloroethyl
1-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl 938
2,2,2-trichloroethyl 1-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl
939 2,2,2-trichloroethyl 1-methyl-3-trifluoromethyl-4-methoxy
carbonylpyrazol-5-yl 940 2,2,2-trichloroethyl
1-(3-chloropyridine-2-yl)-3-bromopyrazol-5-yl 941
2,2,2-trichloroethyl 1-(3-chloropyridin-2-yl)-3-bromo-
4-chloropyrazol-5-yl 942 2,2,2-trichloroethyl
2-heptafluoroisopropyl-4-methylpyridin-5-yl 943
2,2,2-trichloroethyl 2-{1,1,1,3,3,3-hexafluoro
isopropyloxy}pyridin-5-yl 944 2,2,2-trichloroethyl
2-(1,1,1,3,3,3-hexafluoroisopropyloxy)- 4-methylpyridin-5-yl 945
2,2,2-trichloroethyl 2-chloro-4-methylpyridin-5-yl 946
2,2,2-trichloroethyl 3-chloro-5-trifluoromethylpyridin-2-yl 947
2,2,2-trichloroethyl 2-bromo-4-methyl-6-chloropyridin-3-yl 948
2,2,2-trichloroethyl 2-bromo-6-(1,1,1,3,3,3-hexafluoro-
isopropyloxy)pyridin-3-yl 949 2,2,2-trichloroethyl
2,6-dichloro-4-(trifluoromethylsulfinyl)phenyl 950
2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfinyl)phenyl
951 2,2,2-trichloroethyl
2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl 952
2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfinyl)phenyl
953 2,2,2-trichloroethyl
2,6-dichloro-4-(pentafluoroethylsulfonyl)phenyl 954
2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfonyl)phenyl
955 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propyl
sulfinyl)phenyl 956 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 957
2,2,2-trichloroethyl 2-chloro-6-methyl-4-(nonafluoro-2-butyl)phenyl
958 2,2,2-trichloroethyl
2-bromo-6-methyl-4-(nonafluoro-2-butyl)phenyl 959
2,2,2-trichloroethyl 2-iodo-6-methyl-4-(nonafluoro-2-butyl)phenyl
960 2,2,2-trichloroethyl 2,6-dichloro-4-(nonafluoro-2-butyl)phenyl
961 2,2,2-trichloroethyl 2,6-dibromo-4-(nonafluoro-2-butyl)phenyl
962 2,2,2-trichloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 963
2,2,2-trichloroethyl 2,6-dichloro-4-pentafluoroethylphenyl 964
2,2,2-trichloroethyl 2,6-dimethyl-4-(pentafluoroethylthio) phenyl
965 2,2,2-trichloroethyl 2,6-dimethyl-4-(pentafluoroethylsulfinyl)
phenyl 966 2,2,2-trichloroethyl
2,6-dimethyl-4-(pentafluoroethylsulfonyl) phenyl 967
2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylthio) phenyl
968 i-Pr 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 969 cyclobutyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 970 cyclopentyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 971 4-cyanobenzyl
2-chloro4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 972 2-methoxyethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 973 2-cyanoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 974 2-(methylthio)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 975 2-(ethylthio)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 976 1-methyl-2-(methylthio)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 977 2-(ethylsulfinyl)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 978 2-(ethylsulfonyl)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 979 2-fluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 980 2,2-difluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 981 2,2,2-trifluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 982 1,3-difluoro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 983 1-chloro-3-fluoro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 984 1-methyl-2,2,2-trifluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 985 3,3,3-trifluoro-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 986 2,2,3,3,3-pentafluoro-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 987 3,3,4,4,4-pentafluoro-2-butyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 988 4,4,4-trifluoro-n-butyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 989 2,2,3,3-tetrafluorocyclobutyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 990 2-chloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 991 2,2-dichloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 992 2,2,2-trichloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 993 1,3-dichloro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 994 3-chloro-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 995 2-bromoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 996 2,2,2-tribromoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 997 3-bromo-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 998 2-iodoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 999 tetrahydrofuran-3-yl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1000 (furan-2-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1001 (furan-3-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1002 (tetrahydrofuran-2-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1003 (tetrahydrofuran-3-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1004 (thiophen-2-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1005 (thiophen-3-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1006 (pyridin-2-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1007 (pyridin-3-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1008 (6-chloropyridin-3-yl)methyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1009 Et
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1010 i-Pr
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1011 vinyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1012 propargyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1013 cyclobutyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1014 cyclopentyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1015 benzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1016 3-cyanobenzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1017 4-cyanobenzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1018 3-chlorobenzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1019 2-methoxyethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1020 2-cyanoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1021 2-(methylthio)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1022 2-(ethylthio)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1023 1-methyl-2-(methylthio)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1024 2-(ethylsulfinyl)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1025 2-(ethylsulfonyl)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1026 2-fluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1027 2,2-difluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1028 2,2,2-trifluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1029 1,3-difluoro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1030 1-chloro-3-fluoro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1031 1-methyl-2,2,2-trifluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1032 3,3,3-trifluoro-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1033 2,2,3,3,3-pentafluoro-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1034 3,3,4,4,4-pentafluoro-2-butyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1035 4,4,4-trifluoro-n-butyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1036 2,2,3,3-tetrafluorocyclobutyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1037 2-chloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1038 2,2-dichloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1039 2,2,2-trichloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1040 1,3-dichloro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1041 3-chloro-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1042 2-bromoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1043 2,2,2-tribromoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1044 3-bromo-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1045 2-iodoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1046 tetrahydrofuran-3-yl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1047 (furan-2-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1048 (furan-3-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1049 (tetrahydrofuran-2-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1050 (tetrahydrofuran-3-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1051 (thiophen-2-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1052 (thiophen-3-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1053 (pyridin-2-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1054 (pyridin-3-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1055 (6-chloropyridin-3-yl)methyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1056 Et
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1057 i-Pr 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1058 vinyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1059 propargyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1060 cyclobutyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1061 cyclopentyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1062 benzyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1063 3-cyanobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1064 4-cyanobenzyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1065 3-chlorobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1066 2-methoxyethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1067 2-cyanoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1068 2-(methylthio)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1069 2-(ethylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1070 1-methyl-2-(methylthio)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1071 2-(ethylsulfinyl)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1072 2-(ethylsulfonyl)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1073 2-fluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1074 2,2-difluoroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1075 2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1076 1,3-difluoro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1077 1-chloro-3-fluoro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1078 1-methyl-2,2,2-trifluoroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1079 3,3,3-trifluoro-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1080 2,2,3,3,3-pentafluoro-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1081 3,3,4,4,4-pentafluoro-2-butyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1082 4,4,4-trifluoro-n-butyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1083 2,2,3,3-tetrafluorocyclobutyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1084 2-chloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1085 2,2-dichloroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1086 2,2,2-trichloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1087 1,3-dichloro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1088 3-chloro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1089 2-bromoethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1090 2,2,2-tribromoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1091 3-bromo-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl
1092 2-iodoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1093 tetrahydrofuran-3-yl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1094 (furan-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1095 (furan-3-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1096 (tetrahydrofuran-2-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1097 (tetrahydrofuran-3-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1098 (thiophen-2-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1099 (thiophen-3-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1100 (pyridin-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1101 (pyridin-3-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1102 (6-chloropyridin-3-yl)methyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1103 Et 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1104 i-Pr
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1105 vinyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1106 propargyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1107 cyclobutyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1108 cyclopentyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1109 benzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1110 3-cyanobenzyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1111 4-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1112 3-chlorobenzyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1113 2-methoxyethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1114 2-cyanoethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1115 2-(methylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1116 2-(ethylthio)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1117 1-methyl-2-(methylthio)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1118 2-(ethylsulfinyl)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1119 2-(ethylsulfonyl)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1120 2-fluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1121 2,2-difluoroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1122 2,2,2-trifluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1123 1,3-difluoro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1124 1-chloro-3-fluoro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1125 1-methyl-2,2,2-trifluoroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1126 3,3,3-trifluoro-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1127 2,2,3,3,3-pentafluoro-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1128 3,3,4,4,4-pentafluoro-2-butyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1129 4,4,4-trifluoro-n-butyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1130 2,2,3,3-tetrafluorocyclobutyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1131 2-chloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1132 2,2-dichloroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1133 2,2,2-trichloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1134 1,3-dichloro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1135 3-chloron-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1136 2-bromoethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1137 2,2,2-tribromoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1138 3-bromo-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1139 2-iodoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1140 tetrahydrofuran-3-yl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1141 (furan-2-1)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1142 (furan-3-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1143 (tetrahydrofuran-2-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1144 (tetrahydrofuran-3-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1145 (thiophen-2-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1146 (thiophen-3-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1147 (pyridin-2-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1148 (pyridin-3-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1149 (6-chloropyridin-3-yl)methyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1150 Et 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1151
i-Pr 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1152
vinyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1153
propargyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl
1154 cyclobutyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1155 cyclopentyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1156 benzyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1157
3-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1158 4-cyanobenzyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1159
3-chlorobenzyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1160 2-methoxyethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1161
2-cyanoethyl 2-bromo-4-methyl6-(heptafluoro isopropyl)pyridin-3-yl
1162 2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1163 2-(ethylthio)ethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1164
1-methyl-2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1165 2-(ethylsulfinyl)ethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1166
2-(ethylsulfonyl)ethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1167 2-fluoroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1168
2,2-difluoroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1169 2,2,2-trifluoroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1170
1,3-difluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1171 1-chloro-3-fluoro-2-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1172
1-methyl-2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1173 3,3,3-trifluoro-n-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1174
2,2,3,3,3-pentafluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1175 3,3,4,4,4-pentafluoro-2-butyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1176
4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1177 2,2,3,3-tetrafluorocyclobutyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1178
2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1179 2,2-dichloroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1180
2,2,2-trichloroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1181 1,3-dichloro-2-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1182
3-chloro-n-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1183 2-bromoethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1184
2,2,2-tribromoethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1185 3-bromo-n-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1186
2-iodoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl
1187 tetrahydrofuran-3-yl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1188 (furan-2-yl)methyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1189
(furan-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1190 (tetrahydrofuran-2-yl)methyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1191
(tetrahydrofuran-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1192 (thiophen-2-yl)methyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1193
(thiophen-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1194 (pyridin-2-yl)methyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1195
(pyridin-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1196 (6-chloropyridin-3-yl)methyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1197 Et
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1198 i-Pr
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1199 vinyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1200 propargyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1201 cyclobutyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1202 cyclopentyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1203 benzyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1204 3-cyanobenzyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1205 4-cyanobenzyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1206 3-chlorobenzyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1207 2-methoxyethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1208 2-cyanoethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1209
2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1210 2-(ethylthio)ethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1211
1-methyl-2-(methylthio)ethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1212
2-(ethylsulfinyl)ethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1213
2-(ethylsulfonyl)ethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1214 2-fluoroethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1215
2,2-difluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1216 2,2,2-trifluoroethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1217
1,3-difluoro-2-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1218
1-chloro3-fluoro-2-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1219
1-methyl-2,2,2-trifluoroethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1220
3,3,3-trifluoro-n-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1221
2,2,3,3,3-pentafluoro-n-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1222
3,3,4,4,4-pentafluoro-2-butyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1223
4,4,4-trifluoro-n-butyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1224
2,2,3,3-tetrafluorocyclobutyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1225 2-chloroethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1226
2,2-dichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1227 2,2,2-trichloroethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1228
1,3-dichloro-2-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1229
3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1230 2-bromoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1231 2,2,2-tribromoethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1232
3-bromo-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1233 2-iodoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1234 tetrahydrofuran-3-yl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1235
(furan-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1236 (furan-3-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1237
(tetrahydrofuran-2-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1238
(tetrahydrofuran-3-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1239
(thiophen-2-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1240
(thiophen-3-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1241
(pyridin-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1242 (pyridin-3-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1243
(6-chloropyridin-3-yl)methyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1244 Et
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1245 i-Pr
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1246 vinyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1247 propargyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1248 cyclobutyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1249 cyclopentyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1250 benzyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1251 3-cyanobenzyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1252 4-cyanobenzyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1253 3-chlorobenzyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1254 2-methoxyethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1255 2-cyanoethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1256
2-(methylthio)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1257 2-(ethylthio)ethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1258
1-methyl-2-(methylthio)ethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1259
2-(ethylsulfinyl)ethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1260
2-(ethylsulfonyl)ethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1261 2-fluoroethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1262
2,2-difluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1263 2,2,2-trifluoroethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1264
1,3-difluoro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1265 1-chloro-3-fluoro-2-propyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1266
1-methyl-2,2,2-trifluoroethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1267
3,3,3-trifluoro-n-propyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1268
2,2,3,3,3-pentafluoro-n-propyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1269
3,3,4,4,4-pentafluoro-2-butyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1270
4,4,4-trifluoro-n-butyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1271
2,2,3,3-tetrafluorocyclobutyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1272 2-chloroethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1273
2,2-dichloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1274 2,2,2-trichloroethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1275
1,3-dichloro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1276 3-chloro-n-propyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1277 2-bromoethyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1278
2,2,2-tribromoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1279 3-bromo-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1280 2-iodoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1281
tetrahydrofuran-3-yl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1282 (furan-2-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1283
(furan-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1284 (tetrahydrofuran-2-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1285
(tetrahydrofuran-3-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1286
(thiophen-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1287 (thiophen-3-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1288
(pyridin-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1289 (pyridin-3-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1290
(6-chloropyridin-3-yl)methyl
2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1291 Et
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1292 i-Pr
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1293 vinyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1294 propargyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1295 cyclobutyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1296 cyclopentyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1297 benzyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1298 3-cyanobenzyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1299 4-cyanobenzyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1300 3-chlorobenzyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1301 2-methoxyethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1302 2-cyanoethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1303
2-(methylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1304 2-(ethylthio)ethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1305
1-methyl-2-(methylthio)ethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1306
2-(ethylsulfinyl)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1307 2-(ethylsulfonyl)ethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1308 2-fluoroethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1309 2,2-difluoroethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1310
2,2,2-trifluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1311 1,3-difluoro-2-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1312
1-chloro-3-fluoro-2-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1313
1-methyl-2,2,2-trifluoroethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1314
3,3,3-trifluoro-n-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1315
2,2,3,3,3-pentafluoro-n-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1316
3,3,4,4,4-pentafluoro-2-butyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1317
4,4,4-trifluoro-n-butyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1318
2,2,3,3-tetrafluorocyclobutyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1319 2-chloroethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1320 2,2-dichloroethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1321
2,2,2-trichloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1322 1,3-dichloro-2-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1323 3-chloro-n-propyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1324 2-bromoethyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1325
2,2,2-tribromoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1326 3-bromo-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1327 2-iodoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1328
tetrahydrofuran-3-yl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1329 (furan-2-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1330
(furan-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1331 (tetrahydrofuran-2-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1332
(tetrahydrofuran-3-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1333
(thiophen-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1334 (thiophen-3-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1335
(pyridin-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1336 (pyridin-3-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1337
(6-chloropyridin-3-yl)methyl
2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1338 Et
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1339 i-Pr
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1340 vinyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1341 propargyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1342 cyclobutyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1343 cyclopentyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1344 benzyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1345 3-cyanobenzyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1346 4-cyanobenzyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1347 3-chlorobenzyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1348 2-methoxyethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1349 2-cyanoethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1350
2-(methylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1351 2-(ethylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1352 1-methyl-2-(methylthio)ethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1353
2-(ethylsulfinyl)ethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1354 2-(ethylsulfonyl)ethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1355 2-fluoroethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1356
2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1357 2,2,2-trifluoroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1358 1,3-difluoro-2-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1359
1-chloro3-fluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1360 1-methyl-2,2,2-trifluoroethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1361
3,3,3-trifluoro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1362 2,2,3,3,3-pentafluoro-n-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1363
3,3,4,4,4-pentafluoro-2-butyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1364 4,4,4-trifluoro-n-butyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1365
2,2,3,3-tetrafluorocyclobutyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1366 2-chloroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1367 2,2-dichloroethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1368
2,2,2-trichloroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1369 1,3-dichloro-2-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1370
3-chloro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1371 2-bromoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1372 2,2,2-tribromoethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1373 3-bromo-n-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1374 2-iodoethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1375
tetrahydrofuran-3-yl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1376 (furan-2-yl)methyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1377
(furan-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1378 (tetrahydrofuran-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1379 (tetrahydrofuran-3-yl)methyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1380
(thiophen-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1361 (thiophen-3-yl)methyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1382
(pyridin-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1383 (pyridin-3-yl)methyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1384
(6-chloropyridin-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl
[0136] TABLE-US-00002 TABLE 2 (1-B) ##STR26## Compound No. X.sub.1
X.sub.2 X.sub.3 X.sub.4 R.sub.1 Q 1385 Me H H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropyl phenyl 1386 Me
H H H i-Pr 2,6-dimethy-4-heptafluoroisopropyl phenyl 1387 Me H H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1388 F H H H Et 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1389 F H
H H i-Pr 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1390 F H H H
vinyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1391 F H H H
propargyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1392 F H H H
cyclobutyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1393 F H H H
cyclopentyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1394 F H H H
benzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1395 F H H H
3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1396 F H H
H 4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1397 F H
H H 3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1398
F H H H 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1399 F H H H 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropyl
phenyl 1400 F H H H 2-(methylthio)ethyl
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1401 F H H H
2-(ethylthi)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1402 F
H H H 1-methyl-2-(methylthio)-
2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl 1403 F H H H
2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1404 F H H H 2-(ethylsulfonyl)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1405 F H H H
2-fluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1406 F H H
H 2,2-difluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1407
F H H H 2,2,2-trifluoroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1408 F H H H
1,3-difluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1409 F H H H 1-chloro-3-fluoro-2-
2,6-dimethyl-4-heptafluoroisopropylphenyl propyl 1410 F H H H
1-methyl-2,2,2-trifluoro 2,6-dimethyl-4-heptafluoroisopropylphenyl
ethyl 1411 F H H H 3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1412 F H H H
2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-heptafluoroisopropylphenyl
propyl 1413 F H H H 3,3,4,4,4-pentafluoro-2-
2,6-dimethyl-4-heptafluoroisopropylphenyl butyl 1414 F H H H
4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1415 F H H H 2,2,3,3-tetrafluoro
2,6-dimethyl-4-heptafluoroisopropylphenyl cyclobutyl 1416 F H H H
2-chloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1417 F H H
H 2,2-dichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1418
F H H H 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1419 F H H H
1,3-dichloro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1420 F H H H 3-chloro-n-propyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1421 F H H H 2-bromoethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1422 F H H H
2,2,2-tribromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1423
F H H H 3-bromo-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1424 F H H H 2-idoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1425 F H H H tetrahydrofuran-3-yl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1426 F H H H
(furan-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1427 F
H H H (furan-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1428 F H H H (tetrahydrofuran-2-
2,6-dimethyl-4-heptafluoroisopropylphenyl yl)methyl 1429 F H H H
(tetrahydrofuran-3- 2,6-dimethyl-4-heptafluoroisopropylphenyl
yl)methyl 1430 F H H H (thiophen-2-yl)methyl
2,6-dimethyl-4-heprafluoroisopropylphenyl 1431 F H H H
(thiophen-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1432 F H H H (pyridin-2-yl)methyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1433 F H H H
(pyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1434
F H H H (6-chloropyridin-3-
2,6-dimethyl-4-heptafluoroisopropylphenyl yl)methyl 1435 F H H H Et
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1436 F H H H i-Pr
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1437 F H H H vinyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1438 F H H H propargyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1439 F H H H cyclobutyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1440 F H H H cyclopentyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1441 F H H H benzyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1442 F H H H
3-cyanobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1443 F H H
H 4-cyanobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1444 F H
H H 3-chlorobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1445 F
H H H 2-methoxyethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1446
F H H H 2-cyanoethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1447
F H H H 2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl)
phenyl 1448 F H H H 2-(ethylthio)ethyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1449 F H H H
1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl)
phenyl 1450 F H H H 2-(ethylsulfinyl)ethyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1451 F H H H
2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl
1452 F H H H 2-fluoroethyl 2,6-dimethyl-4-(nonefluoro2-butyl)
phenyl 1453 F H H H 2,2-difluoroethyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1454 F H H H
2,2,2-trifluoroethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1455
F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-(nonafluoro2-butyl)
phenyl 1456 F H H H 1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1457 F H H H
1-methyl-2,2,2-trifluoro 2,6-dimethyl-4-(nonafluoro2-butyl) ethyl
phenyl 1458 F H H H 3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1459 F H H H
2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-(nonafluoro2-butyl) propyl
phenyl 1460 F H H H 3,3,4,4,4-pentafluoro-2-
2,6-dimethyl-4-(nonafluoro2-butyl) butyl phenyl 1385 Me H H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1386 Me
H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1387 Me H H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1388
F H H H Et 2,6-dimethyl-4-heptafluoroisopropylphenyl 1389 F H H H
i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1390 F H H H vinyl
2,6-dimethyl-4-hepsafluoroisopropylphenyl 1391 F H H H propargyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1392 F H H H cyclobutyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1393 F H H H cyclopentyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1394 F H H H benzyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1395 F H H H
3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1396 F H H
H 4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1397 F H
H H 3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1398 F
H H H 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1399
F H H H 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1400
F H H H 2-(methylthio)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1401 F H H H
2-(ethylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1402 F
H H H 1-methyl-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl
(methylthio)ethyl 1403 F H H H 2-(ethylsulfinyl)ethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1404 F H H H
2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1481 F H H H (6-chloropyridin-3-yl)
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl methyl 1482 F H H H Et
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1483 F H H H i-Pr
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1484 F H H H vinyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1485 F H H H
cyclobutyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1486 F H
H H cyclopentyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1487 F H H H 3-cyanobenzyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1488 F H H H
4-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1489
F H H H 2-cyanoethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1490 F H H H
2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1491 F H H H 2-(ethylthio)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1492 F H H H
1-methyl-2-(methylthio)
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl ethyl 1493 F H H H
2-(ethylsulfinyl)ethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1494 F H H H
2-fluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1495
F H H H 2,2-difluoroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1496 F H H H
2,2,2-trifluoroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1497 F H H H
1,3-difluoro-2-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1498 F H H H
1-chloro-3-fluoro-2-
2,6-dichloro-4-(heptefluoro-n-propylthio)phenyl propyl 1499 F H H H
1-methyl-2,2,2- 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
trifluoroethyl 1500 F H H H 3,3,3-trifluoro-n-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1501 F H H H
2,2,3,3,3-pentafluoro-n-
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl propyl 1502 F H H H
4,4,4-trifluoro-n-butyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1503 F H H H
2,2,3,3-tetrafluorocyclo
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl butyl 1504 F H H H
2-chloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1505
F H H H 2,2-dichloroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1506 F H H H
2,2,2-trichloroethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1507 F H H H
1,3-dichloro-2-propyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1508 F H H H
3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1509 F H H H 2-bromoethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1510 F H H H
3-bromo-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1511 F H H H 2-iodoethyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1512 F H H H
(6-chloropyridin-3-yl)
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl methyl 1513 F H H H
Et 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1514 F H H H i-Pr
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1515 F H H H vinyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1516 F H H H
cyclobutyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1517 F H H
H cyclopentyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1518 F
H H H 3-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1519 F H H H 4-cyanobenzyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1520 F H H H 2-cyanoethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1521 F H H H
2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1522 F H H H 2-(ethylthio)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1523 F H H H
1-methyl-2-(methythio)
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl ethyl 1524 F H H H
2-(ethylsulfinyl)ethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1525 F H H H
2-fluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1526 F
H H H 2,2-difluoroethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1527 F H H H
2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1528 F H H H 1,3-difluoro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1529 F H H H
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1530 F H H H
2-methyl-2,2,2-trifluoro
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl ethyl 1531 F H H H
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1532 F H H H
2,2,3,3,3-pentafluoro-n-
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl propyl 1533 F H H H
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1534 F H H H
2,2,3,3-tetrafluorocyclo
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl butyl 1535 F H H H
2-chloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1536 F
H H H 2,2-dichloroethyl
2,6-dibromo-4-(trif1uoromethylsulfonyl)phenyl 1537 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1538 F H H H 1,3-dichloro-2-propyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1539 F H H H
3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1540 F H H H 2-bromoethyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1541 F H H H
3-bromo-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1542
F H H H 2-iodoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1543 F H H H (6-chloropyridin-3-
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl yl)methyl 1544 F H H
H Et 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1545 F H H H i-Pr
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1546 F H H H vinyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1547 F H H H cyclobutyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1548 F H H H cyclopentyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1549 F H H H
3-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1550 F H H
H 4-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1551 F H
H H 2-cyanoethyl 2,6-dibromo-4-(pentafluoroerhylthio)phenyl 1552 F
H H H 2-(methylthio)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1553 F H H H
2-(ethylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1554
F H H H 1-methyl-2- 2,6-dibromo-4-(pentafluoroethylthio)phenyl
(methylthio)ethyl 1555 F H H H 2-(ethylsulfinyl)ethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1556 F H H H
2-fluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1557 F H H
H 2,2-difluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1558
F H H H 2,2,2-trifluoroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1559 F H H H
1,3-difluoro2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
1560 F H H H 1-chloro-3-fluoro-2-
2,6-dibromo-4-(pentafluoroethylthio)phenyl propyl 1561 F H H H
1-methyl-2,2,2-trifluoro 2,6-dibromo-4-(pentafluoroethylthio)phenyl
ethyl 1562 F H H H 3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1563 F H H H
2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(pentafluoroethylthio)phenyl
propyl 1564 F H H H 4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1565 F H H H
2,2,3,3-tetrafluoro 2,6-dibromo-4-(pentafluoroethylthio)phenyl
cyclobutyl 1566 F H H H 2-chloroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1567 F H H H
2,2-dichloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1568 F
H H H 2,2,2-trichloroethyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1569 F H H H
1,3-dichloro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
1570 F H H H 3-chloro-n-propyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl 1571 F H H H
2-bromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1572 F H H
H 3-bromo-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1573
F H H H 2-iodoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1574
F H H H (6-chloropyridin-3-yl)
2,6-dibromo-4-(pentafluoroethylthio)phenyl methyl 1575 F H H H Et
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1576 F H H H i-Pr
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1577 F H H H vinyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1578 F H H H
cyclobutyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1579 F H
H H cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1580
F H H H 3-cyanobenzyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1581 F H H H
4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1582 F
H H H 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1583 F H H H 2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1584 F H H H
2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1585 F H H H 1-methyl-2-(methylthio)
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl ethyl 1586 F H H H
2-(ethylsulfinyl)ethyl
2,6-dlbromo-4-(heptafluoro-n-propylthio)phenyl 1587 F H H H
2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1588 F
H H H 2,2-difluoroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1589 F H H H
2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1590 F H H H 1,3-difluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1591 F H H H
1-chloro-3-fluoro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1592 F H H H
1-methyl-2,2,2-trifluoro
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl ethyl 1593 F H H H
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1594 F H H H
2,2,3,3,3-pentafluoro-n-
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl propyl 1595 F H H H
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1596 F H H H
2,2,3,3-tetrafluoro 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
cyclobutyl 1597 F H H H 2-chlooroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1598 F H H H
2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1599 F H H H 2,2,2-trichloroethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1600 F H H H
1,3-dichloro-2-propyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1601 F H H H
3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1602 F H H H 2-bromoethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1603 F H H H
3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1604 F H H H 2-iodoethyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1605 F H H H
(6-chloropyridin-3-yl)
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl methyl 1606 F H H H
Et 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1607 F H H H i-Pr
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1608 F H H H vinyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1609 F H H H
cyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1610 F H
H H cyclopentyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1611
F H H H 3-cyanobenzyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1612 F H H H
4-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1613 F
H H H 2-cyanoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1614 F H H H 2-(methylthio)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1615 F H H H
2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1616 F H H H 1-methyl-2-(methylthio)
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl ethyl 1617 F H H H
2-(ethylsulfinyl)ethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1618 F H H H
2-fluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1619 F
H H H 2,2-difluoroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1620 F H H H
2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1621 F H H H 1,3-difluoro-2-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1622 F H H H
1-chloro-3-fluoro2-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1623 F H H H
1-methyl-2,2,2-trifluoro
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl ethyl 1624 F H H H
3,3,3-trifluoro-n-propyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1625 F H H H
2,2,3,3,3-pentafluoro-n-
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl propyl 1626 F H H H
4,4,4-trifluoro-n-butyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1627 F H H H
2,2,3,3-tetrafluorocyclo
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl butyl 1628 F H H H
2-chloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1629 F
H H H 2,2-dichloroethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1630 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1631 F H H H 1,3-dichloro-2-propyl
2,6-dibromo-4-(heptafluoroisopropylshio)phenyl 1632 F H H H
3-chloro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1633 F H H H 2-bromoethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1634 F H H H
3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1635 F H H H 2-iodoethyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1636 F H H H
(6-chloropyridin-3-yl)
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl methyl 1637 F H H H
Et 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1638 F H H H
i-Pr 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1639 F H H H
vinyl 2,6-dimethyl-4-(heptefluoro-n-propylthio)phenyl 1640 F H H H
cyclobutyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1641 F H
H H cyclopentyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1642 F H H H 3-cyanobenzyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1643 F H H H
4-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1644
F H H H 2-cyanoethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1645 F H H H
2-(methylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1646 F H H H 2-(ethylthio)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1647 F H H H
1-methyl-2-(methylthio)
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl ethyl 1648 F H H H
2-(ethylsulfinyl)ethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1649 F H H H
2-fluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1650
F H H H 2,2-difluoroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1651 F H H H
2,2,2-trifluoroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1652 F H H H
1,3-difluoro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1653 F H H H
1-chloro-3-fluoro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1654 F H H H
1-methyl-2,2,2-trifluoro
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl ethyl 1655 F H H H
3,3,3-trifluoro-n-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1656 F H H H
2,2,3,3,3-pentafluoro-n-
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl propyl 1657 F H H H
4,4,4-trifluoro-n-butyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1658 F H H H
2,2,3,3-tetrafluorocyclo
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
butyl 1659 F H H H 2-chloroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1660 F H H H
2,2-dichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1661 F H H H 2,2,2-trichloroethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1662 F H H H
1,3-dichloro-2-propyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1663 F H H H
3-chloro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1664 F H H H 2-bromoethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1665 F H H H
3-bromo-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1666 F H H H 2-iodoethyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1667 F H H H
(6-chloropyridin-3- 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
yl)methyl 1668 F H H H 2,2,2-trichloroethyl
2,6-dichloro-4-(trifluoromethylsulfinyl)phenyl 1669 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfinyl)phenyl
1670 F H H H 2,2,2-trichloroethyl
2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl 1671 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfinyl)phenyl
1672 F H H H 2,2,2-trichloroethyl
2,6-dichloro-4-(pentafluoroethylsulfonyl)phenyl 1673 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfonyl)phenyl
1674 F H H H 2,2,2-trichloroethyl
2,6-dichloro-4-(heptafluoro-n-propyl sulfinyl)phenyl 1675 F H H H
2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl 1676 F H H H 2,2,2-trichloroethyl
2-chloro-6-methyl-4-(nonafluoro-2-butyl)phenyl 1677 F H H H
2,2,2-trichloroethyl 2-bromo-6-methyl-4-(nonafluoro-2-butyl)phenyl
1678 F H H H 2,2,2-trichloroethyl
2-iodo-6-methyl-4-(nonafluoro-2-butyl)phenyl 1679 F H H H
2,2,2-trichloroethyl 2,6-dichloro-4-(nonafluoro-2-butyl)phenyl 1680
F H H H 2,2,2-trichloroethyl
2,6-dibromo-4-(nonafluoro-2-butyl)phenyl 1681 F H H H Et
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1682 F H H H i-Pr
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1683 F H H H vinyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1684 F H H H cyclobutyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1685 F H H H clopentyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1686 F H H H 3-cyanobenzyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1687 F H H H 4-cyanobenzyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy(pyridin-3-yl 1688 F H H H 2-cyanoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1689 F H H H 2-(methylthio)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1690 F H H H 2-(ethylthio)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1691 F H H H 1-methyl-2-(methylthio)
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1692 F H H H 2-(ethylsulfinyl)ethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1693 F H H H 2-fluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1694 F H H H 2,2-difluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1695 F H H H 2,2,2-trifluoroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1696 F H H H 1,3-difluoro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1697 F H H H 1-chloro-3-fluoro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1698 F H H H 1-methyl-2,2,2-trifluoro
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1699 F H H H 3,3,3-trifluoro-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1700 F H H H 2,2,3,3,3-pentafluoro-n-
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl
isopropyloxy)pyridin-3-yl 1701 F H H H 4,4,4-trifluoro-n-butyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1702 F H H H 2,2,3,3-tetrafluoro
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl
isopropyloxy)pyridin-3-yl 1703 F H H H 2-chloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1704 F H H H 2,2-dichloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1705 F H H H 2,2,2-trichloroethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridln-3-yl 1706 F H H H 1,3-dichloro-2-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1707 F H H H 3-chloro-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1708 F H H H 2-bromoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1709 F H H H 3-bromo-n-propyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy(pyridin-3-yl 1710 F H H H 2-iodoethyl
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy(pyridin-3-yl 1711 F H H H (6-chloropyridin-3-yl)
2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl
isopropyloxy)pyridin-3-yl 1712 F H H H Et
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1713 F H H H i-Pr
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1714 F H H H vinyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1715 F H H H cyclobutyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1716 F H H H cyclopentyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1717 F H H H 3-cyanobenzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1718 F H H H 4-cyanobenzyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy(pyridin-3-yl 1719 F H H H 2-cyanoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy(pyridin-3-yl 1720 F H H H 2-(methylthio)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1721 F H H H 2-(ethylthio)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1722 F H H H 1-methyl-2-(methylthio)
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1723 F H H H 2-(ethylsulfinyl)ethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1724 F H H H 2-fluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1725 F H H H 2,2-difluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1726 F H H H 2,2,2-trifluoroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1727 F H H H 1,3-difluoro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1728 F H H H 1-chloro-3-fluoro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1729 F H H H 1-methyl-2,2,2-trifluoro
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1730 F H H H 3,3,3-trifluoro-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1731 F H H H 2,2,3,3,3-pentafluoro-n-
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl
isopropyloxy)pyridin-3-yl 1732 F H H H 4,4,4-trifluoro-n-butyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1733 F H H H 2,2,3,3-tetrafluoro
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl
isopropyloxy)pyridin-3-yl 1734 F H H H 2-chloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1735 F H H H 2,2-dichloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1736 F H H H 2,2,2-trichloroethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1737 F H H H 1,3-dichloro-2-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1738 F H H H 3-chloro-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1739 F H H H 2-bromoethyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1740 F H H H 3-bromo-n-propyl
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1741 F H H H 2-iodoethyl
2-bromo-4-methyl-6-(2,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1742 F H H H (6-chloropyridin-3-yl)
2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl
isopropyloxy)pyridin-3-yl 1743 F H H H Et
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1744 F H H H i-Pr 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1745 F H H H vinyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1746 F H H H cyclobutyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1747 F H H H cyclopentyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1748 F H H H 3-cyanobenzyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl
1749 F H H H 4-cyanobenzyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1750 F H H H 2-cyanoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1751 F H H H 2-(methylthio)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1752 F H H H 2-(ethylthio)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1753 F H H H 1-methyl-2-(methylthio)
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1754 F H H H 2-(ethylsulfinyl)ethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1755 F H H H 2-fluoroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1756 F H H H 2,2-difluoroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1757 F H H H 2,2,2-trifluoroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1758 F H H H 1,3-difluoro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1759 F H H H 1-chloro-3-fluoro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1760 F H H H 1-methyl-2,2,2-trifluoro
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1761 F H H H 3,3,3-trifluoro-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1762 F H H H 2,2,3,3,3-pentafluoro-n-
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl
isopropyloxy)pyridin-3-yl 1763 F H H H 4,4,4-trifluoro-n-butyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexefluoro isopropyloxy)pyridin-3-yl
1764 F H H H 2,2,3,3-tetrafluoro
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl
isopropyloxy)pyridin-3-yl 1765 F H H H 2-chloroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1766 F H H H 2,2-dichloroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1767 F H H H 2,2,2-trichloroethyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1768 F H H H 1,3-dichloro-2-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1769 F H H H 3-chloro-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1770 F H H H 2-bromoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1771 F H H H 3-bromo-n-propyl
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyioxy)pyridin-3-yl
1772 F H H H 2-iodoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1773 F H H H (6-chloropyridin-3-yl)
2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl
isopropyloxy)pyridin-3-yl 1774 F H H H Et
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1775 F H H H i-Pr 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyioxy)pyridin-3-yl 1776 F H H H vinyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1777 F H H H cyclobutyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1778 F H H H cyclopentyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1779 F H H H 3-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1780 F H H H 4-cyanobenzyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1781 F H H H 2-cyanoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1782 F H H H 2-(methylthio)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1783 F H H H 2-(ethylthio)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1784 F H H H 1-methyl-2-(methylthio)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1785 F H H H 2-(ethylsulfinyl)ethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1786 F H H H 2-fluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1787 F H H H 2,2-difluoroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1788 F H H H 2,2,2-trifluoroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1789 F H H H 1,3-difluoro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1790 F H H H 1-chloro-3-fluoro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1791 F H H H 1-methyl-2,2,2-trifluoro
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro ethyl
isopropyloxy)pyridin-3-yl 1792 F H H H 3,3,3-trifluoro-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1793 F H H H 2,2,3,3,3-pentafluoro-n-
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro propyl
isopropyloxy)pyridin-3-yl 1794 F H H H 4,4,4-trifluoro-n-butyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1795 F H H H 2,2,3,3-tetrafluoro
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl
isopropyloxy)pyridin-3-yl 1796 F H H H 2-chloroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1797 F H H H 2,2-dichloroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1798 F H H H 2,2,2-trichloroethyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1799 F H H H 1,3-dichloro-2-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1800 F H H H 3-chloro-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1801 F H H H 2-bromoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1802 F H H H 3-bromo-n-propyl
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl
1803 F H H H 2-iodoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl 1804 F H H H (6-chloropyridin-3-yl)
2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro methyl
isopropyloxy(pyridin-3-yl 1805 F H H H Et
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1806 F H H H
i-Pr 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1807 F
H H H vinyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl
1808 F H H H cyclobutyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1809 F H H H cyclopentyl
2-bromo-4-methyl-8-(heptafluoro isopropyl)pyridin-3-yl 1810 F H H H
3-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1811 F H H H 4-cyanobenzyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1812 F H H H
2-cyanoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl
1813 F H H H 2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1814 F H H H 2-(ethylthio)ethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1815 F H H H
1-methyl-2-(methylthio) 2-bromo-4-methyl-6-(heptafluoro ethyl
isopropyl)pyridin-3-yl 1816 F H H H 2-(ethylsulfinyl)ethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1817 F H H H
2-fluoroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1818 F H H H 2,2-difluoroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1819 F H H H
2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1820 F H H H 1,3-difluoro-2-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1821 F H H H
1-chloro-3-fluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1822 F H H H 1-methyl-2,2,2-trifluoroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1823 F H H H
3,3,3-trifluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1824 F H H H 2,2,3,3,3-pentafluoro-n-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1825 F H H H
4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1826 F H H H 2,2,3,3-tetrafluorocyclobutyl
2-bromo--methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1827 F H H H
2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1828 F H H H 2,2-dichloroethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1829 F H H H
2,2,2-trichloroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1830 F H H H 1,3-dichloro-2-propyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1831 F H H H
3-chloro-n-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1832 F H H H 2-bromoethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl(pyridin-3-yl 1833 F H H H
3-bromo-n-propyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1834 F H H H 2-iodoethyl
2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1835 F H H H
(6-chloropyridin-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl 1836 F H H H Et 2-chloro-6-methyl-4-
heptafluoroisopropylphenyl 1837 F H H H i-Pr 2-chloro-6-methyl-4-
heptafluoroisopropylphenyl 1838 F H H H vinyl 2-chloro-6-methyl-4-
heptafluoroisopropylphenyl 1839 F H H H cyclobutyl
2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1840 F H H H
cyclopentyl 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1841 F
H H H 3-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl
1842 F H H H 4-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropyl
phenyl 1843 F H H H 2-cyanoethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1844 F H H H
2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl
1845 F H H H 2-(ethylthio)ethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1846 F H H H
1-methyl-2-(methylthio) 2-chloro-6-methyl-4-heptafluoroisopropyl
ethyl phenyl 1847 F H H H 2-(ethylsulfinyl)ethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1848 F H H H
2-fluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1849
F H H H 2,2-difluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl
phenyl 1850 F H H H 2,2,2-trifluoroethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1851 F H H H
1,3-difluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropyl
phenyl 1852 F H H H 1-chloro-3-fluoro-2-propyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1853 F H H H
1-methyl-2,2,2- 2-chloro-6-methyl-4-heptafluoroisopropyl
trifluoroethyl phenyl 1854 F H H H 3,3,3-trifluoro-n-propyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1855 F H H H
2,2,3,3,3-pentafluoro-n- 2-chloro-6-methyl-4-heptafluoroisopropyl
propyl phenyl 1856 F H H H 4,4,4-trifluoro-n-butyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1857 F H H H
2,2,3,3-tetrafluoro 2-chloro-6-methyl-4-heptafluoroisopropyl
cyclobutyl phenyl 1858 F H H H 2-chloroethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1859 F H H H
2,2-dichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl
1860 F H H H 2,2,2-trichloroethyl
2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1861 F H H H
1,3-dichloro-2-propyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1862 F H H H
3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1863 F H H H 2-bromoethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1864 F H H H
3-bromo-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1865 F H H H 2-iodoethyl
2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1866 F H H H
(6-chloropyridin-3-yl)
2-chloro-6-methyl-4-heptafluoroisopropylphenyl methyl 1867 F H H H
Et 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1868 F H H H
i-Pr 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1869 F H H H
vinyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1870 F H H H
cyclobutyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1871 F H
H H cyclopentyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1872 F H H H 3-cyanobenzyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1873 F H H H 4-cyanobenzyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1874 F H H H
2-cyanoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1875 F
H H H 2-(methylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1876 F H H H 2(ethylthio)ethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1877 F H H H
1-methyl-2-(methylthio) 2-iodo-6-n-propyl-4-heptafluoro
ethyl isopropylphenyl 1878 F H H H 2-(ethylsulfinyl)ethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1879 F H H H
2-fluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1880
F H H H 2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1881 F H H H 2,2,2-trifluoroethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1882 F H H H
1,3-difluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1883 F H H H 1-chloro-3-fluoro-2-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1884 F H H H
1-methyl-2,2,2-trifluoro 2-iodo-6-n-propyl-4-heptafluoro ethyl
isopropylphenyl 1885 F H H H 3,3,3-trifluoro-n-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1886 F H H H
2,2,3,3,3-pentafluoro-n- 2-iodo-6-n-propyl-4-heptafluoro propyl
isopropylphenyl 1887 F H H H 4,4,4-trifluoro-n-butyl
2-iodo-8-n-propyl-4-heptafluoro isopropylphenyl 1888 F H H H
2,2,3,3-tetrafluoro 2-iodo-6-n-propyl-4-heptafluoro cyclobutyl
isopropylphenyl 1889 F H H H 2-chloroethyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1890 F H H H
2,2-dichloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1891 F H H H 2,2,2-trichloroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1892 F H H H 1,3-dichloro-2-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1893 F H H H
3-chloro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
1894 F H H H 2-bromoethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1895 F H H H 3-bromo-n-propyl
2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1896 F H H H
2-iodoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1897 F
H H H (6-chloropyridin-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl 1898 Cl H H H i-Pr
2-methyl-4-heptafluoroisopropylphenyl 1899 Cl H H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1900 Cl
H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1901 Cl H H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1902
Cl H H H 2,2,2-trichloroethyl 2,4-bistrifluoromethylphenyl 1903 Cl
H H H 2,2,2-trichloroethyl 2-(1,1,1,3,3,3-hexafluoroisopropyloxy)-
4-methylpyridin-5-yl 1904 Br H H H i-Pr
2,6-dimethyl-4-heptafluoroisopropylphenyl 1905 Br H H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1906
F F H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
1907 F F H H 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1908 F F F H i-Pr
2,6-dimethyl-4-heptafluoroisopropylphenyl 1909 H Me H H i-Pr
2-methyl-4-heptafluoroisopropylphenyl 1910 H Me H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1911 H
Me H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1912 H Me H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1913
H MeO H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1914 H MeO H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1915 H F
H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1916 H F H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1917 H F
H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1918 H F H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1919
H Cl H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1920 H Cl H H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1921 H
Cl H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1922 H Cl H H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1923
H H Me H 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1924 H H CF.sub.3 H i-Pr
2-methyl-4-heptafluoroisopropylphenyl 1925 H H CF.sub.3 H
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1926 H H
CF.sub.3 H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1927 H H
CF.sub.3 H 2,2,2-trichloroethyl
2,6-dimethyl-4-heptafluoroisopropylphenyl 1928 H H NH.sub.2 H i-Pr
2,6-dimethyl-4-heptafluoroisopropylphenyl 1929 H H Me.sub.2N H
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1930
H H H Me i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1931 H H H Me
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1932 H H
H Me i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1933 H H H Me
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1934
H H H F i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1935 H H H F
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1936 H H
H F i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1937 H H H F
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1938
H H H Cl i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1939 H H H Cl
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1940 H H
H Cl i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1941 H H H Cl
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1942
H H H Br i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1943 H H H Br
2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1944 H H
H I 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1945
H H H I i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1946 H H H I
t-Bu 2-methyl-4-heptafluoroisopropylphenyl 1947 H H H I
2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
[0137] TABLE-US-00003 TABLE 3 (1-C) ##STR27## Compound No. X.sub.1
X.sub.2 X.sub.3 X.sub.4 R.sub.1 R.sub.2 R.sub.3 Q 1948 H H H H
2,2,2-trichloro Me H 2,6-dibromo-4-(heptafluoro ethyl
n-propylthio)phenyl 1949 H H H H 2,2,2-trichloro H Me
2-methyl-4-heptafluoroisopropyl ethyl phenyl 1950 H H H H i-Pr H Me
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1951 H H H H
2,2,2-trichloro H Me 2,6-dimethyl-4-heptafluoroisopropyl ethyl
phenyl 1952 H H H H i-Pr H Me 2-methyl-6-chloro-4-
heptafluoroisopropyl phenyl 1953 H H H H 2,2,2-trichloro H Me
2-methyl-6-chloro-4- ethyl heptafluoroisopropyl phenyl 1954 H H H H
i-Pr H Me 2-methyl-6-bromo-4-heptafluoroisopropyl phenyl 1955 H H H
H 2,2,2-trichloro H Me 2-methyl-6-bromo-4-heptafluoroisopropyl
ethyl phenyl 1956 H H H H 2,2,2-trichloro H Et
2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1957 H H H H
2,2,2-trichloro H i-Pr 2,6-dimethyl-4-heptafluoroisopropyl ethyl
phenyl 1958 H H H H 2,2,2-trichloro Me H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1959 F H H H
2,2,2-trichloro Me H 2,6-dimethyl-4-heptafluoroisopropyl ethyl
phenyl 1960 H H MeNH H i-Pr Me H
2,6-dimethyl-4-heptafluoroisopropyl phenyl
[0138] TABLE-US-00004 TABLE 4 (1-D) ##STR28## Compound No. G.sub.1
G.sub.2 G.sub.3 R.sub.1 Q 1961 O S O Me
2,6-dimethyl-4-heptafluoroisopropylphenyl 1962 O S O Et
2,6-dimethyl-4-heptafluoroisopropylphenyl 1963 O O S iPr
2,6-dimethyl-4-heptafluoroisopropylphenyl 1964 O O S
2,2,2-trichLoro 2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl
[0139] TABLE-US-00005 TABLE 5 (1-E) ##STR29## Compound No. A.sub.1
A.sub.2 A.sub.3 A.sub.4 R.sub.1 R.sub.2 Q 1965 N C C C i-Pr H
2-methyl-4-heptafluoroisopropylphenyl 1966 N C C C
2,2,2-trichloroethyl H 2-methyl-4-heptafluoroisopropylphenyl 1967 N
C C C i-Pr H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1968 N C C
C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1969 N C C C 2-chloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl
phenyl 1970 N C C C 2-fluoroethyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1971 N C C C Et H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1972 N C C C vinyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1973 N C C C cyclobutyl
H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1974 N C C C
cyclopentyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1975 N C C
C 3-cyanobenzyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1976 N
C C C 4-cyanobeozyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1977 N C C C 2-cyanoethyl H 2,6-dimethyl-4-heptafluoroisopropyl
phenyl 1978 N C C C 2-(methylthio)ethyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1979 N C C C
2-(ethylthio)ethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1980 N C C C 1-methyl-2- H 2,6-dimethyl-4-heptafluoroisopropyl
(methylthio)ethyl phenyl 1981 N C C C 2-(ethylsulfinyl)ethyl H
2,6-dimethyl-4-heptatluoroisopropyl phenyl 1982 N C C C
2-fluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1983 N C
C C 2,2-difluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1984 N C C C 2,2,2-trifluoroethyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1985 N C C C
1,3-difluoro-2-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1986 N C C C 1-chloro-3-fluoro-2- H
2,6-dimethyl-4-heptafluoroisopropyl propyl phenyl 1987 N C C C
1-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-heptafluoroisopropyl
ethyl phenyl 1988 N C C C 3,3,3-trifluoro-n-propyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1989 N C C C
2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-heptatluoroisopropyl
propyl phenyl 1990 N C C C 4,4,4-trifluoro-n-butyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1991 N C C C
2,2,3,3-tetrafluoro H 2,6-dimethyl-4-heptafluoroisopropyl
cyclobutyl phenyl 1992 N C C C 2,2-dichloroethyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1993 N C C C
1,3-dichloro-2-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1994 N C C C 3-chloro-n-propyl H
2,6-dimethyl-4-heptafluoroisopropyl phenyl 1995 N C C C
2-bromoethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1996 N C
C C 3-bromo-n-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1997 N C C C 2-iodoethyl H 2,6-dimethyl-4-heptafluoroisopropyl
phenyl 1998 N C C C (6-chloropyridin-3-yl) H
2,6-dimethyl-4-heptafluoroisopropyl methyl phenyl 1999 N C C C Et H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2000 N C C C i-Pr H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2001 N C C C vinyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2002 N C C C cyclobutyl
H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2003 N C C C
cyclopentyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2004 N C C
C 3-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2005 N
C C C 4-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) 2006 N C
C C 2-cyanoethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2007
N C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl)
phenyl 2008 N C C C 2-(ethylthio)ethyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2009 N C C C
1-methyl-2-(methylthio) H 2,6-dimethyl-4-(nonafluoro-2-butyl) ethyl
phenyl 2010 N C C C 2-(ethylsulfinyl)ethyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2011 N C C C
2-fluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2012 N C
C C 2,2-difluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl
2013 N C C C 2,2,2-trifluoroethyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2014 N C C C
1,3-difluoro-2-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl
2015 N C C C 1-chloro-3-fluoro-2-propyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2016 N C C C
1-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-(nonafluoro-2-butyl)
ethyl phenyl 2017 N C C C 3,3,3-trifluoro-n-propyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2018 N C C C
2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-(nonafluoro-2-butyl)
propyl phenyl 2019 N C C C 4,4,4-trifluoro-n-butyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2020 N C C C
2,2,3,3-tetrafluoro H 2,6-dimethyl-4-(nonafluoro-2-butyl)
cyclobutyl phenyl 2021 N C C C 2-chloroethyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2022 N C C C
2,2-dichloroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2023
N C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl)
phenyl 2024 N C C C 1,3-dichloro-2-propyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2025 N C C C
3-chloro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2026
N C C C 2-bromoethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl
2027 N C C C 3-bromo-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl)
phenyl 2028 N C C C 2-iodoethyl H
2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2029 N C C C
(6-chloropyridin-3-yl) H 2,6-dimethyl-4-(nonafluoro-2-butyl) methyl
phenyl 2030 N C C C Et H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2031 N C C C i-Pr H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2032 N C C C vinyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2033 N C C C
cyclobutyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2034 N
C C C cyclopentyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2035 N C C C 3-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2036 N C C C 4-cyanobenzyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2037 N C C C
2-cyanoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2038
N C C C 2-(methylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2039 N C C C 2-(ethylthio)ethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2040 N C C C
1-methyl-2-(methylthio) H 2,6-dibromo4-(heptafluoro-n- ethyl
propylthio)phenyl 2041 N C C C 2-(ethylsulfinyl)ethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2042 N C C C
2-fluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2043 N C C C 2,2-difluoroethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2044 N C C C 2,2,2-trifluoroethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2045 N C C C
1,3-difluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2046 N C C C 1-chloro-3-fluoro-2-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2047 N C C C
1-methyl-2,2,2-trifluoro H 2,6-dibromo-4-(heptafluoro-n- ethyl
propylthio)phenyl 2048 N C C C 3,3,3-trifluoro-n-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2049 N C C C
2,2,3,3,3-pentafluoro-n- H 2,6-dibromo-4-(heptafluoro-n- propyl
propylthio)phenyl 2050 N C C C 4,4,4-trifluoro-n-butyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2051 N C C C
2,2,3,3-tetrafluoro H 2,6-dibromo-4-(heptefluoro-n- cyclobutyl
propylthio)phenyl 2052 N C C C 2-chloroethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2053 N C C C
2,2-dichloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2054 N C C C 2,2,2-trichloroethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2055 N C C C 1,3-dichloro-2-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2056 N C C C
3-chloro-n-propyl H 2,6-dibromo-4-(heptafluoro-n propylthio)phenyl
2057 N C C C 2-bromoethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2058 N C C C 3-bromo-n-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2059 N C C C
2-iodoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2060
N C C C (6-chloropyridin-3-yl) H 2,6-dibromo-4-(heptafluoro-n-
methyl propylthio)phenyl 2061 N-oxide C C C i-Pr H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2062 N-oxide C C C
2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2063 N-oxide C C C Et H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2064 N-oxide C C C vinyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2065 N-oxide C C C cyclobutyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2066 N-oxide C C C
cyclopentyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2067
N-oxide C C C 3-cyanobenzyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2068 N-oxide C C C 4-cyanobenzyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2069 N-oxide C C C
2-cyanoethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2070
N-oxide C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2071 N-oxide C C C 2-(ethylthio)ethyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2072 N-oxide C C C
1-methyl-2-(methylthio)ethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2073 N-oxide C C C 2-(ethylsulfinyl)ethyl H
2,6-dimethyl-4-hepcafluoro isopropylphenyl 2074 N-oxide C C C
2-fluoroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2075
N-oxide C C C 2,2-difluoroethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2076 N-oxide C C C 2,2,2-trifluoroethyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2077 N-oxide C C C
1,3-difluoro-2-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2078 N-oxide C C C 1-chloro-3-fluoro-2-propyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2079 N-oxide C C C
1-methyl-2,2,2-trifluoroethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2080 N-oxide C C C 3,3,3-trifluoro-n-propyl H
2,6-dimethyl-4-heptafluoro
isopropylphenyl 2081 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H
2,6-dimethyl-4-heptafluoro propyl isopropylphenyl 2082 N-oxide C C
C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2083 N-oxide C C C 2,2,3,3-tetrafluoro H
2,6-dimethyl-4-heptafluoro cyclobutyl isopropylphenyl 2084 N-oxide
C C C 2-chloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2085 N-oxide C C C 2,2-dichloroethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2086 N-oxide C C C 1,3-dichloro-2-propyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2087 N-oxide C C C
3-chloro-n-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2088
N-oxide C C C 2-bromoethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2089 N-oxide C C C 3-bromo-n-propyl H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2090 N-oxide C C C
2-iodoethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2091
N-oxide C C C (6-chloropyridin-3-yl) H 2,6-dimethyl-4-heptafluoro
methyl isopropylphenyl 2092 N-oxide C C C Et H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2093 N-oxide C C C i-Pr
H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2094 N-oxide C C C
vinyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2095 N-oxide C C
C cyclobutyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2096
N-oxide C C C cyclopentyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2097 N-oxide C C C 3-cyanobenzyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2098 N-oxide C C C
4-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2099
N-oxide C C C 2-cyanoethyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2100 N-oxide C C C 2-(methylthio)ethyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2101 N-oxide C C C
2-(ethylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl
2102 N-oxide C C C 1-methyl-2-(methylthio) H
2,6-dimethyl-4-(nonafluoro-2- ethyl butyl)phenyl 2103 N-oxide C C C
2-(ethylsulfinyl)ethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl
2104 N-oxide C C C 2-fluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2105 N-oxide C C C 2,2-difluoroethyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2106 N-oxide C C C
2,2,2-trifluoroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl
2107 N-oxide C C C 1,3-difluoro-2-propyl H
2,6-dimethyl-4-nonafluoro-2- butyl)phenyl 2108 N-oxide C C C
1-chloro-3-fluoro-2-propyl H 2,6-dimethyl-4-nonafluoro-2-
butyl)phenyl 2109 N-oxide C C C 1-methyl-2,2,2-trifluoro H
2,6-dimethyl-4-(nonafluoro-2- ethyl butyl)phenyl 2110 N-oxide C C C
3,3,3-trifluoro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2111 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H
2,6-dimethyl-4-(nonafluoro-2- propyl butyl)phenyl 2112 N-oxide C C
C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2113 N-oxide C C C 2,2,3,3-tetrafluoro H
2,6-dimethyl-4-(nonafluoro-2- cyclobutyl butyl)phenyl 2114 N-oxide
C C C 2-chloroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl
2115 N-oxide C C C 2,2-dichloroethyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2116 N-oxide C C C
2,2,2-trichloroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl
2117 N-oxide C C C 1,3-dichloro-2-propyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2118 N-oxide C C C
3-chloro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2119
N-oxide C C C 2-bromoethyl H 2,6-dimethyl-4-(nonafluoro-2-
butyl)phenyl 2120 N-oxide C C C 3-bromo-n-propyl H
2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2121 N-oxide C C C
2-iodoethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2122
N-oxide C C C (6-chloropyridin-3-yl) H
2,6-dimethyl-4-(nonafluoro-2- methyl butyl)phenyl 2123 N-oxide C C
C Et H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2124 N-oxide
C C C i-Pr H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2125
N-oxide C C C vinyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2126 N-oxide C C C cyclobutyl H
2,6-dibromo-4-(heprafluoro-n- propylthio)phenyl 2127 N-oxide C C C
cyclopentyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2128
N-oxide C C C 3-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2129 N-oxide C C C 4-cyanobenzyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2130 N-oxide C C C
2-cyanoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2131
N-oxide C C C 2-(methylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2132 N-oxide C C C 2-(ethylthio)ethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2133 N-oxide C C C
1-methyl-2-(methylthio) H 2,6-dibromo-4-(heptafluoro-n- ethyl
propylthio)phenyl 2134 N-oxide C C C 2-(ethylsulfinyl)ethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2135 N-oxide C C C
2-fluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2136 N-oxide C C C 2,2-difluoroethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2137 N-oxide C C C
2,2,2-trifluoroethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2138 N-oxide C C C 1,3-difluoro-2-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2139 N-oxide C C C
1-chloro-3-fluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2140 N-oxide C C C 1-methyl-2,2,2-trifluoro H
2,6-dibromo-4-(heptafluoro-n- ethyl propylthio)phenyl 2141 N-oxide
C C C 3,3,3-trifluoro-n-propyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2142 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H
2,6-dibromo-4-(heptafluoro-n- propyl propylthio)phenyl 2143 N-oxide
C C C 4,4,4-trifluoro-n-butyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2144 N-oxide C C C 2,2,3,3-tetrafluoro H
2,6-dibromo-4-(heptafluoro-n- cyclobutyl propylthio)phenyl 2145
N-oxide C C C 2-chloroethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2146 N-oxide C C C 2,2-dichloroethyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2147 N-oxide C C C
2,2,2-trichloroethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2148 N-oxide C C C 1,3-dichloro-2-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2149 N-oxide C C C
3-chloro-n-propyl H 2,6-dibromo-4-(heptatluoro-n- propylthio)phenyl
2150 N-oxide C C C 2-bromoethyl H 2,6-dibromo-4-(heptafluoro-n-
propylthio)phenyl 2151 N-oxide C C C 3-bromo-n-propyl H
2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2152 N-oxide C C C
2-iodoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2153
N-oxide C C C (6-chloropyridin-3-yl) H
2,6-dibromo-4-(heptafluoro-n- methyl propylthio)phenyl 2154 C N C C
i-Pr H 2-methyl-4- heptafluoroisopropylphenyl 2155 C N C C
2,2,2-trichloroethyl H 2-methyl-4- heptatluoroisopropylphenyl 2156
C N C C i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2157 C N
C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2158 C C N C i-Pr H 2-methyl-4-heptafluoro
isopropylphenyl 2159 C C N C 2,2,2-trichloroethyl H
2-methyl-4-heptafluoro isopropylphenyl 2160 C C N C i-Pr H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2161 C C N C
2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2162 C C C N i-Pr H 2-methyl-4-heptafluoro isopropylphenyl 2163 C C
C N 2,2,2-trichloroethyl H 2-methyl-4-heptafluoro isopropylphenyl
2164 C C C N i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2165
C C C N 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro
isopropylphenyl 2166 C C C N-oxide i-Pr H
2,6-dimethyl-4-heptafluoro isopropylphenyl 2167 C C C N-oxide
2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl
2168 N C C C 2,2,2-trichloroethyl Me 2,6-dimethyl-4-heptafluoro
isopropylphenyl
[0140] TABLE-US-00006 TABLE 6 (4-A) ##STR30## Compound No. R.sub.3
Y.sub.1 Y.sub.2 Y.sub.3 Y.sub.4 Y.sub.5 I-1 H Me H
heptafluoro-n-propyl H Me I-2 H H H heptafluoroisopropyl H H I-3 H
H Me heptafluoroisopropyl H H I-4 H H MeO heptafluoroisopropyl H H
I-5 H H Cl heptafluoroisopropyl H H I-6 H Me H heptafluoroisopropyl
H H I-7 H Me H heptafluoroisopropyl H Me I-8 H Me H
heptafluoroisopropyl H phenyl I-9 H Me H heptafluoroisopropyl Me H
I-10 H Me Me heptafluoroisopropyl H H I-11 H Me Me
heptafluoroisopropyl H Cl I-12 H Me I heptafluoroisopropyl H Cl
I-13 Me Me H heptafluoroisopropyl H Me I-14 i-Pr Me H
heptafluoroisopropyl H Me I-15 H Et H heptafluoroisopropyl H H I-16
H Et H heptafluoroisopropyl H Me I-17 H Et H heptafluoroisopropyl H
Et I-18 H Et H heptafluoroisopropyl H I I-19 H n-Pr H
heptafluoroisopropyl H H I-20 H i-Pr H heptafluoroisopropyl H Me
I-21 H MeO H heptafluoroisopropyl H Me I-22 H Cl H
heptafluoroisopropyl H Et I-23 H Cl H heptafluoroisopropyl Me H
I-24 H Cl H heptafluoroisopropyl MeO H I-25 H Cl Me
heptafluoroisopropyl H Me I-26 H Br H heptafluoroisopropyl H Me
I-27 H Br H heptafluoroisopropyl H Et I-28 H Br H
heptafluoroisopropyl H n-Pr I-29 H Br H heptafluoroisopropyl H n-Bu
I-30 H Br Me heptafluoroisopropyl H Me I-31 H I H
heptafluoroisopropyl H Me I-32 H I H heptafluoroisopropyl H n-Pr
I-33 H Me H nonafluoro-n-butyl H Me I-34 H Me H nonafluoro-2-butyl
H Me I-35 H H H trifluoromethylthio H H I-36 H Br H
trifluoromethylthio H Br I-37 H H H trifluoromethylsulfonyl H H
I-38 H Br H trifluoromethyisulfonyl H Br I-39 H Me H
2,2,2-trifluoroethoxy H H I-40 H H H heptafluoroisopropylthio H H
I-41 H Cl H heptafluoroisopropylthio H Cl I-42 H Br H
heptafluoroisopropylthio H Br I-43 H Cl H heptafluoro-n-propylthio
H Cl I-44 H Br H heptafluoro-n-propylthio H Br I-45 H Cl H
heptafluoroisopropylsulfonyl H Cl I-46 H Br H
nonafluoro-n-butylthio H Br I-47 H Br H pentafluoroethylthio H Br
I-48 H Br H heptafluoro-n-propylsulfinyl H Br I-49 Me Me H
heptafluoro-n-propylthio H Me I-50 Me Br H heptafluoro-n-propylthio
H Br
[0141] TABLE-US-00007 TABLE 7 (4-B) ##STR31## Compound No. X.sub.1
X.sub.2 X.sub.3 X.sub.4 Y.sub.1 Y.sub.3 Y.sub.5 I-51 Me H H H Me
heptafluoroisopropyl H I-52 Me H H H Me heptafluoroisopropyl Me
I-53 H Me H H Me heptafluoroisopropyl H I-54 H Me H H Me
heptafluoroisopropyl Me I-55 H H H Me Me heptafluoroisopropyl H
I-56 H H H Me Me heptafluoroisopropyl Me I-59 F H H H Me
heptafluoroisopropyl Me I-60 F H H H Me heptafluoroisopropylthio Me
I-61 H F H H Me heptafluoroisopropyl Me I-62 H H H F Me
heptafluoroisopropyl H I-63 H H H F Me heptafluoroisopropyl Me I-64
Cl H H H Me heptafluoroisopropyl H I-65 Cl H H H Me
heptafluoroisopropyl Me I 66 H Cl H H Me heptafluoroisopropyl H
I-67 H Cl H H Me heptafluoroisopropyl Me I-68 H H H Cl Me
heptafluoroisopropyl H I-69 H H H Cl Me heptafluoroisopropyl Me
I-70 Br H H H Me heptafluoroisopropyl Me I-71 H H H Br Me
heptafluoroisopropyl H I-72 H I H H Me heptafluoroisopropyl H I-73
H H H I Me heptafluoroisopropyl H I-74 H H H I Me
heptafluoroisopropyl Me I-75 H H CF.sub.3 H Me heptafluoroisopropyl
H I-76 H H CF.sub.3 H Me heptafluoroisopropyl Me I-77 H MeO H H Me
heptafluoroisopropyl H I-78 H H NH.sub.2 H Me heptafluoroisopropyl
H I-79 H H NH.sub.2 H Me heptafluoroisopropyl Me I-80 Cl Cl H Cl Me
heptafluoroisopropyl H
[0142] TABLE-US-00008 TABLE 8 (4-C) ##STR32## Compound No. X.sub.1
X.sub.2 X.sub.3 X.sub.4 Q I-81 H H H H
2-methyl-4-heptafluoroisopropyl-1-naphthyl I-82 H H H H
4-heptafluoroisopropyl-5,6,7,8-tetrahydro-1-naphthyl I-83 H H H H
2-chloro-4-heptafluoroisopropyl-5,6,7,8,s-tetrahydro-1-naphthyl
I-84 H H H H 2-((1,1,1,3,3,3-hexafluoro2-propyloxy)pyridin-5-yl
I-85 Cl H H H
2-(1,1,1,3,3,3-hexafluoro-2-propyloxy)-4-methylpyridin-5-yl I-86 H
H H H 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro-
2-propyloxy)pyridin-3-yl
[0143] Table 9 shows the physical properties of the compounds
represented by formulae (1) and (4) of the present invention. This
table also shows .sup.1H-NMR shift values obtained by using
tetramethylsilane as an internal reference material, and
chloroform-d as a solvent. TABLE-US-00009 TABLE 9 Compound No.
.sup.1H-NMR(CDCl.sub.3, ppm) 3 .delta. 1.30(6H, d, J=6.3Hz),
2.41(3H, s), 5.00-5.05(1H, m), 6.92(1H, s), 7.40-7.61(5H, m),
7.93(1H, s), 8.01(1H, s), 8.21(1H, d, J=8.8Hz) 4 .delta. 0.96(3H,
t, J=7.3Hz), 1.38-1.47(2H, m), 1.63-1.71(2H, m), 2.41(3H, s),
4.19(2H, t, J=6.6Hz), 6.83(1H, s), 7.42-7.62(5H, m), 7.83(1H, s),
8.00(1H, s), 8.25(1H, d, J=8.5Hz) 5 .delta. 0.98(6H, d, J=6.8Hz),
1.94-2.05(1H, m), 2.42(3H, s), 3.98(2H, d, J=6.6Hz), 6.81(1H, s),
7.44-7.52(3H, m), 7.55-7.61(2H, m), 7.85(1H, s), 8.01(1H, s),
8.25(1H, d, J=8.6Hz) 6 .delta. 0.96(3H, t, J=7.6Hz), 1.29(3H, d,
J=6.1Hz), 1.58-1.73(2H, m), 2.42(3H, s), 4.83-4.92(1H, m), 6.72(1H,
s), 7.42-7.61(5H, m), 7.79(1H, s), 8.01(1H, s), 8.26(1H, d,
J=8.5Hz) 7 .delta. 1.53(9H, s), 2.41(3H, s), 6.66(1H, s),
7.40-7.59(5H, m), 7.80(1H, s), 7.98(1H, d, J=1.7Hz), 8.23(1H, d,
J=8.8Hz) 8 .delta. 0.98(9H, s), 2.41(3H, s), 3.89(2H, s), 6.94(1H,
s), 7.41-7.50(3H, m), 7.54-7.57(1H, m), 7.62(1H, d, J=8.1Hz),
7.86(1H, s), 8.02(1H, s), 8.24(1H, d, J=8.8Hz) 9 .delta. 0.97(9H,
s), 1.62(2H, t, J=7.6Hz), 2.41(3H, s), 4.25(2H, t, J=7.6Hz),
6.79(1H, br), 7.42-7.51(3H, m), 7.54-7.57(1H, m), 7.61(1H, d),
7.82(1H, s), 7.99(1H, s), 8.24(1H, d, J=8.5Hz) 10 .delta. 0.90(3H,
t, J=7.3Hz), 0.91(3H, t, J=7.3Hz), 1.26-1.41(8H, m), 1.55-1.65(1H,
m), 2.40(3H, s), 4.10(2H, t, J=5.4Hz), 7.01(1H, s), 7.40-7.50(3H,
m), 7.55(1H, d, J=7.8Hz), 7.62(1H, d, J=7.8Hz), 7.91(1H, s),
8.01(1H, s), 8.21(1H, d, J=8.5Hz) 11 .delta. 2.42(3H, s), 4.55(1H,
dd, J=1.7Hz, 6.3Hz), 4.83(1H, dd, J=1.7Hz, 13.9Hz), 7.29(1H, dd,
J=6.3Hz, 13.9Hz), 7.42-7.50(3H, m), 7.61-7.63(1H, m), 7.77(1H, d,
J=7.8Hz), 8.08(1H, s), 8.15(1H, d, J=7.8Hz), 8.30(1H, s), 8.92(1H,
br-s) 12 .delta. 2.42(3H, s), 4.68-4.70(2H, m), 5.27-5.31(1H, m),
5.35-5.41(1H, m), 5.93-6.03(1H, m), 6.83(1H, br), 7.44-7.52(3H, m),
7.55-7.63(2H, m), 7.79(1H, br), 8.00(1H, s), 8.26(1H, d, J=8.8Hz)
13 .delta. 0.82(3H, d, J=7.1Hz), 0.84-0.99(7H, m), 1.02-1.12(2H,
m), 1.36-1.42(1H, m), 1.50-1.59(1H, m), 1.68-1.72(2H, m),
1.94-1.99(1H, m), 2.11(1H, d, J=1.7Hz), 2.42(3H, s), 4.65-4.72(1H,
m), 6.74(1H, s), 7.42-7.62(5H, m), 7.80(1H, s), 8.02(1H, s),
8.25(1H, d, J=8.5Hz) 14 .delta. 2.38(3H, s), 5.19(2H, s), 7.19(1H,
s), 7.32-7.61(10H, m), 7.91(1H, s), 8.00(1H, s), 8.18(1H, d,
J=8.5Hz) 16 .delta. 2.34(3H, s), 5.27(2H, s), 6.96(1H, br-s),
7.40-7.58(6H, m), 7.63-7.69(3H, m), 7.79(1H, s), 8.00(1H, s),
8.25(1H, d, J=8.8Hz) 17 .delta. 2.33(3H, s), 3.34(3H, s),
3.57-3.61(2H, m), 4.26-4.32(2H, m), 7.13(1H, s), 7.32-7.42(3H, m),
7.46-7.53(2H, m), 7.83(1H, s), 7.91(1H, d, J=1.7Hz), 8.13(1H, d,
J=8.5Hz) 18 .delta. 2.42(3H, s), 5.83(2H, s), 7.16(1H, br-s),
7.43-7.52(3H, m), 7.61(1H, d, J=8.1Hz), 7.68(1H, d, J=8.1Hz),
7.82(1H, s), 8.03(1H, s), 8.25(1H, d, J=8.5Hz) 18 .delta. 2.42(3H,
s), 5.83(2H, s), 7.16(1H, br-s), 7.43-7.52(3H, m), 7.61(1H, d,
J=8.1Hz), 7.68(1H, d, J=8.1Hz), 7.82(1H, s), 8.03(1H, s), 8.25(1H,
d, J=8.5Hz) 19 .delta. 2.40(3H, s), 3.74(2H, t, J=5.6Hz), 4.44(2H,
t, J=5.6Hz), 7.19(1H, s), 7.42-7.50(3H, m), 7.55-7.58(1H, m),
7.63(1H, d, J=7.6Hz), 7.88(1H, s), 8.01(1H, s), 8.22(1H, d,
J=8.8Hz) 20 .delta. 2.40(3H, s), 4.83(2H, s), 7.42-7.49(3H, m),
7.58-7.61(1H, m), 7.67-7.69(2H, m), 7.98(1H, s), 8.06(1H, s),
8.19(1H, d, J=8.5Hz) 21 .delta. 2.43(3H, s), 6.90(1H, s), 7.22(1H,
br-s), 7.47-7.54(3H, m), 7.64-7.68(2H, m), 7.78(1H, s), 8.06(1H,
s), 8.26(1H, d, J=8.8Hz) 22 .delta. 2.01(6H, s), 2.42(3H, s),
6.95(1H, br), 7.44-7.52(3H, m), 7.57-7.62(2H, m), 7.80(1H, s),
8.02(1H, s), 8.24(1H, d, J=8.5Hz) 23 .delta. 2.41(3H, s),
7.23-7.29(1H, m), 7.40-7.55(7H, m), 7.61-7.64(1H, m), 7.72(1H, d,
J=8.3Hz), 7.78(1H, s), 8.07(1H, s), 8.26(1H, d, J=8.8Hz) 24 .delta.
2.36(3H, s), 2.40(3H, s), 7.05-7.09(2H, m), 7.15(1H, s), 7.20(2H,
d, J=8.1Hz), 7.47-7.52(3H, m), 7.60-7.63(1H, m), 7.66-7.68(1H, m),
7.79(1H, s), 8.07(1H, s), 8.25(1H, d, J=8.8Hz) 25 .delta. 2.41(3H,
s), 7.12-7.17(2H, m), 7.32-7.38(2H, m), 7.42-7.48(3H, m), 7.64(1H,
d, J=7.8Hz), 7.82(1H, d, J=7.8Hz), 7.99(1H, d, J=8.5Hz), 8.06(1H,
d, J=8.5Hz), 8.51(1H, s), 9.52(1H, s) 59 .delta. 2.32(6H, s),
3.79(3H, s), 6.92(1H, br-s), 7.34(2H, s), 7.43(1H, t, J=7.8Hz),
7.52-7.62(3H, m), 8.00(1H, s) 60 .delta. 1.33(3H, t, J=7.1Hz),
2.33(6H, s), 4.24(2H, q, J=7.1Hz), 6.80(1H, s), 7.35(2H, s),
7.44(1H, t, J=7.8Hz), 7.46(1H, s), 7.52-7.61(2H, m), 8.02(1H, s) 61
.delta. 0.99(3H, t, J=7.3Hz), 1.71(2H, m), 2.34(6H, s), 4.14(2H, t,
J=6.9Hz), 6.79(1H, s), 7.35(2H, s), 7.41-7.47(2H, m), 7.59-7.61(2H,
m), 8.02(1H, s) 62 .delta. 1.31(6H, d, J=6.3Hz), 2.33(6H, s),
5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.35(2H, s), 7.43(1H, t,
J=8.1Hz), 7.52(1H, s), 7.56-7.61(2H, m), 8.03(1H, s) 63 .delta.
0.96(3H, t, J=7.3Hz), 1.38-1.48(2H, m), 1.61-1.71(2H, m), 2.34(6H,
s), 4.19(2H, t, J=6.9Hz), 6.76(1H, s), 7.35(2H, s), 7.42-7.46(2H,
m), 7.58-7.61(2H, m), 8.02(1H, s) 64 .delta. 0.98(6H, d, J=6.8Hz),
1.94-2.04(1H, m), 2.34(6H, s), 3.97(2H, d, J=6.6Hz), 6.79(1H, s),
7.35(2H, s), 7.42-7.47(2H, m), 7.59-7.61(2H, m), 8.02(1H, s) 66
.delta. 1.53(9H, s), 2.34(6H, s), 6.62(1H, s), 7.35(2H, s),
7.38-7.45(2H, m), 7.51-7.60(2H, m), 8.02(1H, s) 67 .delta. 0.99(9H,
s), 2.34(6H, s), 3.90(2H, s), 6.79(1H, s), 7.35(2H, s), 7.43(1H,
br-s), 7.46(1H, t, J=8.1Hz), 7.59-7.63(2H, m), 8.03(1H, s) 68
.delta. 0.95(3H, d, J=6.8Hz), 0.96(3H, d, J=6.8Hz), 1.24(3H, d,
J=6.3Hz), 1.81-1.89(1H, m), 2.34(6H, s), 4.75(1H, quint, J=6.3Hz),
6.77(1H, s), 7.35(2H, s), 7.44(1H, t, J=8.1Hz), 7.54-7.62(3H, m),
8.05(1H, s) 69 .delta. 0.94(3H, t, J=7.3Hz), 1.29(3H, d, J=6.3Hz),
1.32-1.45(2H, m), 1.46-1.58(1H, m), 1.61-1.70(1H, m), 2.35(6H, s),
4.93(1H, sext., J=6.3Hz), 6.73(1H, s), 7.35(2H, s), 7.42-7.47(1H,
m), 7.51(1H, s), 7.56-7.62(2H, m), 8.05(1H, s) 70 .delta. 0.93(3H,
d, J=6.6Hz), 0.94(3H, d, J=6.6Hz), 1.29(3H, d, J=6.3Hz),
1.31-1.37(1H, m), 1.57-1.75(2H, m), 2.34(6H, s), 4.96-5.05(1H, m),
6.70(1H, s), 7.35(2H, s), 7.42-7.46(2H, m), 7.57-7.61(2H, m),
8.04(1H, s) 71 .delta. 0.97(9H, s), 1.62(2H, t, J=7.6Hz), 2.34(6H,
s), 4.25(2H, t, J=7.6Hz), 6.73(1H, s), 7.35(2H, s), 7.43-7.47(2H,
m), 7.59-7.61(2H, m), 8.02(1H, s) 72 .delta. 1.27-1.34(2H, m),
1.50-1.66(4H, m), 1.74-1.83(2H, m), 2.18-2.32(1H, m), 2.34(6H, s),
4.07(2H, d, J=7.1Hz), 6.79(1H, s), 7.35(2H, s), 7.43-7.51(2H, m),
7.58-7.62(2H, m), 8.03(1H, s) 73 .delta. 1.62(3H, d, J=6.6Hz),
2.33(6H, s), 5.90(1H, q, J=6.6Hz), 6.82(1H, br-s), 7.28-7.45(9H,
m), 7.56(1H, d, J=8.1Hz), 7.60(1H, d, J=7.6Hz), 8.02(1H, br-s) 74
.delta. 2.34(6H, s), 3.02(2H, t, J=7.1Hz), 4.42(2H, t, J=7.1Hz),
6.74(1H, br-s), 7.23-7.27(2H, m), 7.31-7.35(5H, m), 7.41-7.47(2H,
m), 7.58-7.62(2H, m), 7.99(1H, br-s) 75 .delta. 2.34(6H, s),
4.58(1H, dd, J=2.0Hz, 6.3Hz), 4.87(1H, dd, J=2.0Hz, 13.9Hz),
7.00(1H, s), 7.25(1H, dd, J=6.3Hz, 13.9Hz), 7.35(2H, s), 7.47(1H,
t, J=7.8Hz), 7.55(1H, s), 7.63-7.65(2H, m), 8.03(1H, s) 76 .delta.
2.34(6H, s), 4.68-4.70(2H, m), 5.26-5.31(1H, m), 5.35-5.41(1H, m),
5.92-6.02(1H, m), 6.84(1H, s), 7.35(2H, s), 7.42-7.47(2H, m),
7.60-7.62(2H, m), 8.02(1H, s) 77 .delta. 2.33(6H, s), 2.53(1H, t,
J=1.4Hz), 4.79(2H, d, J=1.4Hz), 6.97(1H, br-s), 7.35(2H, s),
7.44(1H, t, J=8.1Hz), 7.51(1H, s), 7.59-7.63(2H, m), 8.02(1H, s) 78
.delta. 1.60-1.70(1H, m), 1.78-1.86(1H, m), 2.07-2.18(2H, m),
2.33(6H, s), 2.35-2.43(2H, m), 5.00-5.08(1H, m), 6.80(1H, s),
7.35(2H, s), 7.41-7.46(1H, m), 7.53-7.62(3H, m), 8.03(1H, s) 79
.delta. 1.68-1.80(6H, m), 1.86-1.94(2H, m), 2.34(6H, s),
5.20-5.23(1H, m), 6.72(1H, s), 7.35(2H, s), 7.42-7.62(4H, m),
8.04(1H, s) 81 .delta. 2.32(6H, s), 5.22(2H, s), 6.87(1H, s),
7.34(2H, s), 7.36-7.45(7H, m), 7.57-7.61(2H, m), 8.01(1H, s) 82
.delta. 2.33(9H, s), 5.18(2H, s), 6.83(1H, br-s), 7.14-7.20(3H, m),
7.31(1H, d, J=7.8Hz), 7.35(2H, s), 7.44(2H, t, J=7.8Hz),
7.52-7.62(2H, m), 8.01(1H, br-s) 83 .delta. 2.34(6H, s), 5.28(2H,
s), 6.90(1H, br-s), 7.35(2H, s), 7.43-7.54(4H, m), 7.61-7.66(4H,
m), 8.01(1H, s) 84 .delta. 2.34(6H, s), 5.24(2H, s), 6.92(1H,
br-s), 7.35-7.52(4H, m), 7.63-7.81(6H, m), 8.02(1H, s) 85 .delta.
2.34(6H, s), 5.27(2H, s), 6.97(1H, br-s), 7.35(2H, s),
7.45-7.52(4H, m), 7.61-7.69(4H, m), 8.01(1H, s) 89 .delta. 2.34(6H,
s), 5.34(2H, s), 6.90(1H, br), 7.28-7.30(3H, m), 7.35(2H, s),
7.39-7.49(3H, m), 7.59-7.64(2H, m), 8.04(1H, m) 90 .delta. 2.33(6H,
s), 5.18(2H, s), 6.92(1H, s), 7.22-7.34(5H, m), 7.40-7.47(3H, m),
7.59-7.63(2H, m), 8.02(1H, s) 91 .delta. 2.33(6H, s), 5.18(2H, s),
6.86(1H, s), 7.29-7.38(6H, m), 7.43-7.47(2H, m), 7.60-7.62(2H, m),
8.01(1H, s) 92 .delta. 2.34(6H, s), 5.32(2H, s), 6.92(1H, br-s),
7.36(2H, s), 7.42(1H, s), 7.48(1H, t, J=7.8Hz), 7.58(2H, d,
J=9.0Hz), 7.62-7.66(2H, m), 8.01(1H, s), 8.25(2H, d, J=9.0Hz) 93
.delta. 2.35(6H, s), 3.93(3H, s), 5.28(2H, s), 6.88(1H, br-s),
7.36(2H, s), 7.41(1H, s), 7.45-7.49(4H, m), 7.63(2H, d, J=6.8Hz),
8.02(1H, s), 8.05(1H, d, J=6.8Hz) 94 .delta. 2.32(6H, s), 2.62(1H,
br), 3.87(2H, t, J=4.4Hz), 4.29-4.32(2H, m), 7.26(1H, s), 7.34(2H,
s), 7.42(1H, t, J=8.1Hz), 7.54-7.61(2H, m), 7.77(1H, s), 8.00(1H,
s) 95 .delta. 2.31(6H, s), 3.41(3H, s), 3.64-3.66(2H, m),
4.32-4.35(2H, m), 7.14(1H, s), 7.34(2H, s), 7.40(1H, t, J=7.8Hz),
7.55-7.60(2H, m), 7.67(1H, s), 8.00(1H, s) 96 .delta. 1.23(3H, t,
J=6.8Hz), 2.29(6H, s), 3.56(2H, q, J=6.8Hz), 3.67-3.70(2H, m),
4.31-4.34(2H, m), 7.26(1H, s), 7.33(2H, s), 7.38-7.40(1H, m),
7.52-7.60(2H, m), 7.83(1H, s), 8.00(1H, s) 97 .delta. 1.18(6H, d,
J=6.1Hz), 2.29(6H, s), 3.63-3.69(3H, m), 4.30-4.32(2H, m), 7.26(1H,
s), 7.33(2H, s), 7.38(1H, t, J=7.8Hz), 7.56-7.60(2H, m), 7.82(1H,
s), 8.00(1H, s) 98 .delta. 2.28(6H, s), 3.70-3.73(2H, m),
4.33-4.36(2H, m), 4.57(2H, s), 7.23-7.39(9H, m), 7.53(1H, d,
J=7.8Hz), 7.58(1H, d, J=7.8Hz), 7.87(1H, s), 7.99(1H, s) 99 .delta.
1.20(3H, t, J=8.1Hz), 1.95-2.00(2H, m), 2.35(6H, s), 3.47-3.57(4H,
m), 4.30(2H, t, J=6.6Hz), 6.78(1H, s), 7.35(2H, s), 7.46(2H, t,
J=7.8Hz), 7.61(2H, d, J=7.8Hz), 8.02(1H, s) 100 .delta. 1.30(3H, t,
J=7.3Hz), 2.34(6H, s), 4.26(2H, q, J=7.3Hz), 4.72(2H, s), 7.35(2H,
s), 7.36-7.40(1H, m), 7.52-7.60(3H, m), 7.77-7.79(1H, m), 7.90(1H,
br-s) 101 .delta. 1.56(3H, d, J=7.3Hz), 2.33(6H, s), 3.79(3H, s),
5.18(1H, q, J=7.3Hz), 7.21(1H, br), 7.35(2H, s), 7.41(1H, t,
J=7.8Hz), 7.55-7.62(3H, m), 7.98(1H, s) 102 .delta. 1.29(3H, t,
J=6.8Hz), 1.55(3H, d, J=6.8Hz), 2.34(6H, s), 4.23(2H, q, J=6.8Hz),
5.16(1H, q, J=6.8Hz), 7.24(1H, br), 7.35(2H, s), 7.41(1H, t,
J=7.8Hz), 7.55-7.62(3H, m), 7.96(1H, s) 103 .delta. 2.21(3H, s),
2.34(6H, s), 2.84(2H, t, J=6.1Hz), 4.46(2H, t, J=6.1Hz), 6.91(1H,
br-s), 7.35(2H, s), 7.43(1H, t, J=7.8Hz), 7.52-7.70(3H, m),
8.01(1H, s) 104 .delta. 2.10(3H, s), 2.34(6H, s), 4.33-4.42(4H, m),
6.97(1H, br-s), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.57-7.64(3H,
m), 8.01(1H, s) 106 .delta. 2.33(6H, s), 2.78(2H, t, J=6.3Hz),
4.40(2H, t, J=6.3Hz), 7.12(1H, br), 7.35(2H, s), 7.45(1H, t,
J=7.8Hz), 7.60-7.65(3H, m), 8.01(1H, s) 108 .delta. 2.17(3H, s),
2.34(6H, s), 2.80(2H, t, J=6.6Hz), 4.37(2H, t, J=6.6Hz), 6.84(1H,
br-s), 7.35(2H, s), 7.43-7.52(2H, m), 7.58-7.63(2H, m), 8.02(1H, s)
109 .delta. 1.25-1.31(3H, m), 2.33(6H, s), 2.57-2.64(2H, m),
2.81-2.85(2H, m), 4.32-4.38(2H, m), 6.92(1H, s), 7.35(2H, s),
7.42-7.49(1H, m), 7.58-7.63(3H, m), 8.03(1H, s) 110 .delta.
1.28(6H, d, J=6.6Hz), 2.34(6H, s), 2.84(2H, t, J=7.1Hz),
2.94-3.04(1H, m), 4.34(2H, t, J=7.1Hz), 6.88(1H, s), 7.35(2H, s),
7.42-7.49(1H, m), 7.52-7.64(3H, m), 8.02(1H, s) 111 .delta.
1.40(3H, d, J=6.1Hz), 2.17(3H, s), 2.34(6H, s), 2.67(1H, dd,
J=6.1Hz, 13.7Hz), 2.77(1H, dd, J=6.1Hz, 13.7Hz), 5.08(1H, sextett.,
J=6.1Hz), 6.80(1H, s), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.52(1H,
s), 7.57-7.63(2H, m), 8.04(1H, s) 112 .delta. 1.24-1.37(3H, m),
2.35(6H, s), 2.26-2.31(2H, m), 2.98-3.06(2H, m), 4.67-4.76(2H, m),
7.35(3H, s), 7.45(2H, t, J=7.8Hz), 7.55-7.74(2H, m), 8.08(1H, br-s)
113 .delta. 1.36-1.43(3H, m), 2.35(6H, s), 3.04-3.10(2H, m),
3.37(2H, t, J=5.9Hz), 4.68-4.73(2H, m), 7.00(1H, br-s), 7.35(2H,
s), 7.46(2H, t, J=7.8Hz), 7.55-7.70(2H, m), 8.02-8.07(1H, m) 116
.delta. 2.35(6H, s), 4.45(2H, dt, J=28.3Hz, 4.0Hz), 4.66(2H, dt,
J=47.3Hz, 4.0Hz), 6.88(1H, br-s), 7.36(2H, s), 7.46-7.50(2H, m),
7.59-7.65(2H, m), 8.02(1H, s) 117 .delta. 2.34(6H, s), 4.38(2H, dt,
J=3.9Hz, 13.6Hz), 6.00(1H, tt, J=3.9Hz, 47.3Hz), 7.05(1H, br-s),
7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.57-7.66(3H, m), 8.01(1H,
s)
118 .delta. 2.33(6H, s), 4.57(2H, q, J=8.3Hz), 7.09(1H, br),
7.35(2H, s), 7.45-7.50(2H, m), 7.61-7.66(2H, m), 8.01(1H, s) 119
.delta. 2.35(6H, s), 4.61-4.75(4H, m), 5.18-5.31(1H, m), 6.98(1H,
br-s), 7.36(2H, s), 7.45-7.52(2H, m), 7.58-7.66(2H, m), 8.03(1H, s)
120 .delta. 2.35(6H, s), 3.75-3.83(2H, m), 4.46-4.80(2H, m),
5.19-5.24(1H, m), 6.97(1H, br-s), 7.36(2H, s), 7.36-7.48(2H, m),
7.60-7.66(2H, m), 8.03(1H, s) 121 (DMSO-d.sub.6).delta. 1.48(3H, d,
J=6.6Hz), 2.35(6H, s), 5.35(1H, septet, J=6.6Hz), 7.33(2H, s),
7.42(1H, t, J=7.8Hz), 7.68(1H, d, J=7.8Hz), 7.76(1H, d, J=7.8Hz),
8.11(1H, s), 8.76(1H, s), 9.26(1H, s) 122
(CDCl.sub.3+DMSO-d.sub.6).delta. 2.35(6H, s), 5.87(1H, septet,
J=6.3Hz), 7.33(2H, s), 7.44(1H, t, J=8.1Hz), 7.71-7.78(2H, m),
8.17(1H, s), 8.97(1H, s), 10.19(1H, s) 123 .delta. 2.34(6H, s),
2.48-2.59(2H, m), 4.42(2H, t, J=6.3Hz), 6.93(1H, br- s), 7.35(2H,
s), 7.46(1H, t, J=7.8Hz), 7.57-7.64(3H, m), 8.01(1H, br-s) 124
.delta. 2.35(6H, s), 4.67(2H, t, J=13.2Hz), 6.98(1H, br-s),
7.29(2H, s), 7.36(1H, s), 7.50(1H, t, J=7.8Hz), 7.65-7.67(2H, m),
8.01(1H, s) 125 .delta. 1.51(3H, d, J=6.4Hz), 2.35(6H, s),
5.49-5.50(1H, m), 6.90(1H, br- s), 7.36(2H, s), 7.44(1H, br-s),
7.50(1H, t, J=7.8Hz), 7.62-7.67(2H, m), 8.02(1H, s) 126 .delta.
1.95-2.05(2H, m), 2.22-2.27(2H, m), 2.35(6H, s), 4.26(2H, t,
J=6.4Hz), 6.81(1H, s), 7.36(2H, s), 7.45-7.49(2H, m), 7.61-7.63(2H,
m), 8.02(1H, s) 127 .delta. 2.35(6H, s), 2.61-2.65(1H, m),
2.9-3.1(1H, m), 5.2-5.3(1H, m), 7.01(1H, br-s), 7.36(2H, s),
7.45-7.52(2H, m), 7.62-7.68(2H, m), 8.01(1H, s) 128 .delta.
2.34(6H, s), 5.84(2H, s), 7.03(1H, s), 7.36(2H, s), 7.44-7.52(2H,
m), 7.65-7.67(2H, m), 8.04(1H, s) 129 .delta. 2.36(6H, s), 7.33(2H,
s), 7.40-7.46(1H, m), 7.65(1H, d, J=7.8Hz), 7.90(1H, d, J=7.8Hz),
7.95(1H, d, J=1.7Hz), 8.55(1H, s), 9.07(1H, s) 130 .delta. 2.35(6H,
s), 3.74-3.77(2H, m), 4.44-4.47(2H, m), 6.87(1H, br), 7.36(2H, s),
7.43-7.52(2H, m), 7.59-7.64(2H, m), 8.02(1H, s) 131 .delta.
2.32(6H, s), 4.53(2H, d, J=5.9Hz), 5.90(1H, t, J=5.9Hz), 7.11(1H,
br-s), 7.35(2H, s), 7.45(1H, t, J=8.1Hz), 7.60-7.64(3H, m),
8.01(1H, br-s) 132 .delta. 2.33(6H, s), 4.84(2H, s), 7.29(1H, br),
7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.58(1H, s), 7.64-7.66(2H, m),
8.04(1H, s) 133 .delta. 2.35(6H, s), 6.90(1H, s), 7.17(1H, br),
7.36(2H, s), 7.42(1H, s), 7.50-7.54(1H, m), 7.66-7.71(2H, m),
8.06(1H, s) 134 .delta. 2.35(6H, s), 3.83(4H, d, J=5.1Hz), 5.22(1H,
quint, J=5.1Hz), 6.93(1H, s), 7.36(2H, s), 7.43(1H, s), 7.48(1H, t,
J=7.8Hz), 7.60-7.66(2H, m), 8.03(1H, s) 135 .delta. 2.01(6H, s),
2.35(6H, s), 6.88(1H, br), 7.36(2H, s), 7.43-7.52(2H, m),
7.58-7.65(2H, m), 8.03(1H, s) 136 .delta. 2.17(2H, quint, J=6.3Hz),
2.34(6H, s), 3.66(2H, t, J=6.3Hz), 4.36(2H, t, J=6.3Hz), 6.83(1H,
s), 7.35(2H, s), 7.43-7.48(1H, m), 7.52(1H, s), 7.59-7.63(2H, m),
8.02(1H, s) 137 .delta. 2.35(6H, s), 3.59(2H, t, J=5.9Hz), 4.51(2H,
t, J=5.9Hz), 6.86(1H, br), 7.36(2H, s), 7.43-7.52(2H, m),
7.60-7.64(2H, m), 8.02(1H, s) 138 .delta. 2.34(6H, s), 5.03(2H, s),
7.15(1H, br), 7.35(2H, s), 7.47-7.54(2H, m), 7.64-7.69(2H, m),
8.06(1H, s) 139 .delta. 2.25(2H, quint, J=6.1Hz), 2.34(6H, s),
3.51(2H, t, J=6.1Hz), 4.35(2H, t, J=6.1Hz), 6.83(1H, s), 7.35(2H,
s), 7.46(1H, t, J=8.1Hz), 7.54(1H, s), 7.58-7.64(2H, m), 8.02(1H,
s) 140 .delta. 2.34(6H, s), 3.34-3.39(2H, m), 4.42-4.47(2H, m),
6.91-6.99(1H, br), 7.35(2H, s), 7.43-7.49(1H, m), 7.56-7.64(3H, m),
8.03(1H, s) 141 (DMSO-d.sub.6).delta. 1.82(3H, s), 2.28(6H, s),
3.33(2H, q, J=5.9Hz), 4.11(2H, t, J=5.9Hz), 7.44(2H, s), 7.46(1H,
d, J=7.8Hz), 7.62-7.69(2H, m), 8.04(1H, t, J=5.9Hz), 8.09(1H, s),
9.90(1H, s), 9.93(1H, s) 146 .delta. 2.34(6H, s), 2.36(3H, s),
7.05-7.08(2H, m), 7.17-7.20(2H, m), 7.33(2H, s), 7.43(1H, t,
J=7.8Hz), 7.68(1H, d, J=7.8Hz), 7.80(1H, d, J=7.8Hz), 8.17(1H, s),
8.67(1H, s), 9.29(1H, s) 147 .delta. 2.35(6H, s), 7.33(2H, s),
7.41-7.57(5H, m), 7.72(1H, d, J=7.8Hz), 7.82(1H, d, J=7.8Hz),
8.18(1H, s), 9.01(1H, s), 9.73(1H, s) 148 .delta. 2.35(6H, s),
7.13-7.18(2H, m), 7.32-7.37(4H, m), 7.41-7.45(1H, m), 7.70(1H, d,
J=7.6Hz), 7.81(1H, d, J=7.6Hz), 8.16(1H, s), 9.04(1H, s), 9.69(1H,
s) 149 .delta. 2.34(6H, s), 7.32(2H, s), 7.33-7.36(1H, m),
7.42-7.52(3H, m), 7.65(1H, d, J=2.4Hz), 7.70(1H, d, J=7.8Hz),
7.80-7.88(4H, m), 8.20(1H, s), 8.76(1H, s), 9.48(1H, s) 154 .delta.
2.08-2.14(1H, m), 2.18-2.30(1H, m), 2.35(6H, s), 3.86-4.01(4H, m),
5.37-5.39(1H, m), 6.87(1H, br-s), 7.35(2H, s), 7.46(2H, t,
J=7.6Hz), 7.58-7.63(2H, m), 8.01(1H, s) 155 .delta. 2.34(6H, s),
5.18(2H, s), 6.38(1H, d, J=3.2Hz), 6.48(1H, d, J=3.2Hz), 6.83(1H,
br-s), 7.35(2H, s), 7.43-7.47(3H, m), 7.57-7.63(2H, m), 8.01(1H, s)
156 .delta. 2.34(6H, s), 5.10(2H, s), 6.48(1H, s), 6.79(1H, br-s),
7.35(2H, s), 7.39-7.47(3H, m), 7.53(1H, s), 7.59-7.63(2H, m),
8.01(1H, br-s) 157 .delta. 1.58-1.67(1H, m), 1.93-1.95(2H, m),
2.01-2.09(1H, m), 2.34(6H, s), 3.78-3.93(2H, m), 4.06-4.23(2H, m),
4.31(1H, dd, J=3.2Hz, 11.2Hz), 6.95(1H, br-s), 7.35(2H, s),
7.45(2H, t, J=7.8Hz), 7.50-7.56(1H, m), 7.63(1H, d, J=7.1Hz),
8.04(1H, s) 158 .delta. 1.66-1.73(1H, m), 2.05-2.13(1H, m),
2.34(6H, s), 2.60-2.70(1H, m), 3.64-3.68(1H, m), 3.73-3.79(1H, m),
3.85-3.92(2H, m), 4.09-4.15(2H, m), 6.87(1H, br-s), 7.35(2H, s),
7.46(2H, t, J=7.8Hz), 7.61-7.66(2H, m), 8.01(1H, br-s) 159 .delta.
2.34(6H, s), 5.38(2H, s), 6.83(1H, br-s), 6.98-7.02(1H, m),
7.16(1H, d, J=2.9Hz), 7.34-7.36(3H, m), 7.43-7.47(2H, m),
7.59-7.63(2H, m), 8.01(1H, s) 160 .delta. 2.34(6H, s), 5.23(2H, s),
6.83(1H, br-s), 7.14(1H, d, J=5.1Hz), 7.33-7.37(4H, m), 7.45(2H, t,
J=7.8Hz), 7.61-7.64(2H, m), 8.02(1H, s) 161 .delta. 2.32(6H, s),
5.34(2H, s), 7.24-7.28(2H, m), 7.35(2H, s), 7.39(1H, d, J=7.8Hz),
7.43(1H, d, J=7.8Hz), 7.55(1H, s), 7.61(2H, t, J=7.8Hz), 7.73(1H,
dt, J=1.7Hz, 7.8Hz), 8.03(1H, s), 8.61(1H, br-s) 162 .delta.
2.36(6H, s), 5.36(2H, s), 6.37(1H, br-s), 6.70(1H, s),
7.31-7.39(4H, m), 7.73-7.82(4H, m), 8.58-8.61(1H, m), 8.72(1H, d,
J=2.0Hz) 163 .delta. 2.34(6H, s), 5.22(2H, s), 6.89(1H, br-s),
7.35-7.49(5H, m), 7.62(2H, d, J=7.3Hz), 7.72-7.77(1H, m), 8.00(1H,
br-s), 8.45(1H, d, J=2.4Hz) 164 .delta.1.23(6H, d, J=6.8Hz),
2.34(3H, s), 3.18(1H, septet, J=6.8Hz), 3.81(3H, s), 6.84(1H, s),
7.36(1H, s), 7.42(1H, s), 7.46(1H, t, J=7.8Hz), 7.56-7.63(3H, m),
8.01(1H, s) 165 .delta.1.22(6H, d, J=6.8Hz), 1.33(3H, t, J=7.3Hz),
2.33(3H, s), 3.17(1H, septet, J=6.8Hz), 4.24(2H, q, J=7.3Hz),
6.80(1H, s), 7.35(1H, s), 7.41(1H, s), 7.44(1H, t, J=7.8Hz),
7.58-7.62(3H, m), 8.02(1H, s) 166 .delta. 1.32(6H, d, J=6.1Hz),
5.03(1H, septet, J=6.1Hz), 6.71(1H, s), 7.40-7.44(1H, m), 7.54(1H,
d, J=2.0Hz), 7.56(1H, d, J=2.0Hz), 7.60(2H, d, J=8.8Hz), 7.80(2H,
d, J=8.8Hz), 7.98(1H, s), 8.03(1H, s) 167 .delta.1.32(6H, d,
J=6.1Hz), 2.53(3H, d, J=8.8Hz), 5.04(1H, septet, J=6.1Hz), 6.71(1H,
br s), 7.41-7.65(6H, m), 7.95-7.97(2H, m) 168 .delta. 1.32(6H, d,
J=6.1Hz), 1.33(3H, t, J=7.6Hz), 2.74(2H, q, J=7.6Hz), 5.04(1H,
septet, J=6.1Hz), 6.70(1H, s), 7.43-7.56(4H, m), 7.60(1H, d,
J=8.1Hz), 7.86(1H, s), 8.00(1H, s), 8.27(1H, d, J=8.5Hz) 169
.delta. 1.02(3H, t, J=7.3Hz), 1.32(6H, d, J=6.3Hz), 1.67-1.77(2H,
m), 2.70(2H, t, J=7.3Hz), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s),
7.43-7.60(5H, m), 7.89(1H, s), 8.03(1H, s), 8.29(1H, d, J=8.5Hz)
170 .delta.1.32(6H, d, J=6.4Hz), 3.89(3H, s), 5.04(1H, septet,
J=6.4Hz), 6.73(1H, br s), 7.05-7.08(1H, m), 7.42-7.46(1H, m),
7.51-7.58(3H, m), 7.80(1H, s), 8.00(1H, s), 8.15(1H, s) 171
.delta.1.32(6H, d, J=6.4Hz), 5.03(1H, septet, J=6.4Hz), 6.75(1H,
s), 7.28-7.47(2H, m), 7.52-7.58(2H, m), 7.72-7.75(1H, m), 7.92(1H,
s), 8.00(1H, s), 8.37(1H, s) 172 .delta.1.31(6H, d, J=6.3Hz),
2.30(3H, s), 2.47(3H, d, J=5.9Hz), 5.01-5.09(1H, m), 6.72(1H,
br-s), 7.40-7.47(2H, m), 7.56-7.60(2H, m), 7.77(1H, d, J=8.6Hz),
7.83(1H, br-s), 8.00(1H, br-s) 173 .delta. 1.31(6H, d, J=6.1Hz),
2.35(3H, s), 2.52(3H, d, J=9.0Hz), 4.99-5.09(1H, m), 6.71(1H,
br-s), 7.30(1H, br-s), 7.44(1H, t, J=7.8Hz), 7.52-7.57(1H, m),
7.61(1H, d, J=7.8Hz), 7.72(1H, s), 7.98(1H, s), 8.06(1H, s) 174
.delta. 1.23(6H, t, J=7.6Hz), 1.32(6H, d, J=6.1Hz), 2.69(4H, q,
J=7.6Hz), 5.03(1H, septet, J=6.1Hz), 6.70(1H, s), 7.38(2H, s),
7.42-7.47(2H, m), 7.58-7.62(2H, m), 8.01(1H, s) 175 .delta.
1.22(3H, t, J=7.6Hz), 1.31(6H, d, J=6.3Hz), 2.34(3H, s), 2.69(2H,
q, J=7.6Hz), 5.03(1H, septet, J=6.3Hz), 6.70(1H, s), 7.37(2H, s),
7.42-7.47(2H, m), 7.58-7.61(2H, m), 8.02(1H, s) 176 .delta.1.22(6H,
d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.33(3H, s), 3.17(1H, septet,
J=6.8Hz), 5.03(1H, septet, J=6.3Hz), 6.76(1H, s), 7.35(1H, s),
7.41(1H, s), 7.44(1H, t, J=8.1Hz), 7.56-7.62(3H, m), 8.03(1H, s)
177 .delta. 1.32(6H, d, J=6.1Hz), 2.35(3H, s), 3.85(3H, s),
5.04(1H, septet, J=6.1Hz), 6.67(1H, s), 6.96(1H, s), 7.13(1H, s),
7.44(1H, t, J=8.1Hz), 7.59-7.65(3H, m), 7.96(1H, s) 178 .delta.
1.30(6H, d, J=6.1Hz), 2.42(3H, s), 5.00(1H, septet, J=6.1Hz),
6.63(1H, s), 7.27-7.41(8H, m), 7.45(1H, s), 7.53(1H, s), 7.58(1H,
d, J=7.8Hz), 7.74(1H, s) 179 .delta.1.31(6H, d, J=6.1Hz), 2.61(3H,
d, J=6.3Hz), 5.05(1H, septet, J=6.1Hz), 6.76(1H, br s),
7.45-7.58(3H, m), 7.70(1H, d, J=8.1Hz), 7.96(1H, t, J=1.8Hz),
8.56-8.58(1H, m), 8.70(1H, br s) 180 .delta. 1.24(3H, t, J=7.6Hz),
1.31(6H, d, J=6.3Hz), 2.75(2H, q, J=7.6Hz), 5.03(1H, septet,
J=6.3Hz), 6.74(1H, s), 7.42-7.47(2H, m), 7.57-7.67(4H, m), 8.02(1H,
s) 181 .delta. 0.93(3H, t, J=7.3Hz), 1.32(6H, d, J=6.1Hz),
1.63-1.71(2H, m), 2.70(2H, t, J=7.6Hz), 5.04(1H, septet, J=6.1Hz),
6.72(1H, s), 7.44-7.48(2H, m), 7.57-7.63(3H, m), 7.68(1H, s),
8.02(1H, s) 182 .delta.1.32(6H, d, J=6.4Hz), 3.92(3H, s), 5.06(1H,
septet, J=6.4Hz), 6.73(1H, s), 7.46-7.50(1H, m), 7.55-7.60(2H, m),
7.69(1H, d, J=7.8Hz), 7.96(1H, s), 8.48(1H, d, J=1.2Hz), 8.58(1H,
s) 183 .delta.1.31(6H, d, J=6.2Hz), 2.30(3H, s), 2.44(3H, d,
J=6.4Hz), 5.01-5.05(1H, m), 6.72(1H, br-s), 7.44-7.48(2H, m),
7.61-7.62(2H, m), 7.78(1H, s), 8.03(1H, br-s) 184 .delta. 1.32(6H,
d, J=6.1Hz), 2.35(3H, s), 2.58(3H, d, J=6.8Hz), 5.01-5.07(1H, m),
6.68(1H, br-s), 7.35(1H, s), 7.46(1H, t, J=7.8Hz), 7.61-7.65(2H,
m), 7.72(1H, s), 8.01(1H, s) 185 .delta.1.31(6H, d, J=6.4Hz),
2.49(3H, s), 4.77(2H, br-s), 5.06(1H, sept, J=6.4Hz), 6.73(1H,
br-s), 7.44-7.49(1H, m), 7.55(1H, s), 7.61-7.63(2H, m), 7.81(1H,
s), 8.05(1H, br-s) 186 .delta.1.32(6H, d, J=6.4Hz), 2.61(3H, s),
5.05(1H, septet), 6.73(1H, br-s), 7.44-7.48(2H, m), 7.57-7.64(2H,
m), 7.95(1H, br-s), 8.06(1H, br-s) 187 .delta. 4.84(2H, s),
7.28(1H, br), 7.45(1H, t, J=8.1Hz), 7.59-7.65(4H, m), 7.81(2H, d,
J=8.5Hz), 7.99(1H, s), 8.17(1H, s) 188 .delta. 2.53(3H, d,
J=8.8Hz), 4.85(2H, s), 7.15(1H, br s), 7.45-7.65(6H, m),
8.00-8.02(2H, m) 189 .delta. 1.34(3H, t, J=7.6Hz), 2.75(2H, q,
J=7.6Hz), 4.85(2H, s), 7.10(1H, s), 7.47-7.52(3H, m), 7.59-7.66(2H,
m), 7.87(1H, s), 8.05(1H, s), 8.27(1H, d, J=8.8Hz) 190 .delta.
1.02(3H, t, J=7.3Hz), 1.67-1.77(2H, m), 2.70(2H, t, J=7.6Hz),
4.85(2H, s), 7.10(1H, br-s), 7.44-7.52(3H, m), 7.59-7.65(2H, m),
7.88(1H, s), 8.07(1H, s), 8.30(1H, d, J=8.5Hz) 191 .delta.3.89(3H,
s), 4.85(2H, s), 7.06(1H, dd, J=8.5Hz, 2.0Hz), 7.18(1H, br s),
7.46-7.54(2H, m), 7.61-7.63(2H, m), 7.79-7.80(1H, m), 8.01(1H, s),
8.10(1H, s) 192 .delta.4.86(2H, s), 7.09(1H, br.), 7.43-7.79(5H,
m), 8.03(1H, br.), 8.56(1H, br), 8.76(1H, d, J=8.8Hz) 193
.delta.4.86(2H, s), 7.16(1H, br s), 7.47-7.74(5H, m), 7.93(1H, s),
8.02(1H, s), 8.23(1H, s) 194 .delta. 2.30(3H, s), 2.47(3H, d,
J=6.0Hz), 4.85(2H, s), 7.12(1H, br- s), 7.42(1H, d, J=9.0Hz),
7.49(1H, t, J=8.1Hz), 7.62-7.67(2H, m), 7.78-7.81(2H, m), 8.03(1H,
br-s) 195 .delta. 2.35(3H, s), 2.52(3H, d, J=8.8Hz), 4.86(2H, s),
7.05(1H, br- s), 7.31(1H, s), 7.50(1H, t, J=7.8Hz), 7.60-7.67(2H,
m), 7.71(1H, s), 8.03(1H, s), 8.07(1H, s) 196 .delta. 1.23(6H, t,
J=7.6Hz), 2.70(4H, q, J=7.6Hz), 4.85(2H, s),
7.03(1H, br), 7.39(3H, s), 7.50(1H, t, J=8.1Hz), 7.65(1H, d,
J=8.1Hz), 7.69(1H, br-s), 8.04(1H, s) 197 .delta. 1.23(3H, t,
J=7.6Hz), 2.35(3H, s), 2.69(2H, q, J=7.6Hz), 4.85(2H, s), 7.05(1H,
br), 7.37(2H, s), 7.42(1H, s), 7.50(1H, t, J=7.8Hz), 7.64-7.66(2H,
m), 8.04(1H, s) 198 .delta.1.23(6H, d, J=6.8Hz), 2.34(3H, s),
3.17(1H, septet, J=6.8Hz), 4.85(2H, s), 7.18(1H, br-s), 7.36(1H,
s), 7.42(1H, s), 7.49(1H, t, J=8.1Hz), 7.55(1H, s), 7.65-7.67(2H,
m), 8.05(1H, s) 199 .delta. 2.36(3H, s), 3.86(3H, s), 4.85(2H, s),
6.96(1H, s), 7.01(1H, br), 7.14(1H, s), 7.49(1H, t, J=8.1Hz),
7.64-7.68(3H, m), 7.99(1H, s) 200 .delta. 2.43(3H, s), 4.83(2H, s),
6.99(1H, br), 7.33-7.42(8H, m), 7.45(1H, s), 7.54(1H, S), 7.64(1H,
d, J=6.3Hz), 7.78(1H, s) 201 .delta. 2.47(3H, s), 4.86(2H, s),
7.06(1H, s), 7.11(1H, br.), 7.24-7.27(1H, m), 7.53(1H, t, J=7.3Hz),
7.66(2H, t, J=7.3Hz), 7.95(1H, s), 8.17(1H, s), 8.85(1H, s) 202
.delta.1.57(3H, s), 4.86(2H, s), 7.10(1H, br s), 7.52(2H, t,
J=7.8Hz), 7.63-7.65(1H, m), 7.72-7.74(1H, m), 8.03(1H, br-s),
8.57-8.59(1H, m), 8.70(1H, br s) 203 .delta. 2.10(3H, s), 4.84(2H,
s), 7.11(1H, d, J=8.8Hz), 7.18-7.22(2H, m), 7.47(1H, t, J=7.8Hz),
7.61(1H, d, J=7.8Hz), 7.65(1H, d, J=7.8Hz), 7.80(1H, br-s),
8.00(1H, br-s) 204 .delta.1.50(9H, s), 2.29(3H, s), 4.85(2H, s),
6.46(1H, br-s), 7.20(1H, br-s), 7.45-7.49(2H, m), 7.50(1H, d,
J=7.3Hz), 7.65(1H, d, J=7.3Hz), 7.88(1H, br-s), 7.99(1H, br-s),
8.19(1H, d, J=8.8Hz) 205 .delta. 1.26(3H, t, J=7.6Hz), 2.76(2H, q,
J=7.6Hz), 4.85(2H, s), 7.06(1H, br), 7.47-7.53(2H, m),
7.58-7.61(2H, m), 7.67-7.69(2H, m), 8.05(1H, s) 206 .delta.
1.25(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz), 4.85(2H, s), 7.06(1H,
br), 7.49-7.53(2H, m), 7.62(1H, s), 7.68-7.70(2H, m), 7.74(1H, s),
8.06(1H, s) 207 .delta. 1.24(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz),
4.86(2H, s), 7.07(1H, br), 7.50-7.58(3H, m), 7.70-7.72(2H, m),
7.96(1H, s), 8.07(1H, s) 208 .delta. 0.93(3H, t, J=7.3Hz),
1.63-1.69(2H, m), 2.70(2H, t, J=7.6Hz), 4.85(2H, s), 7.10(1H, s),
7.45(1H, s), 7.49-7.52(1H, m), 7.53(1H, s), 7.58-7.69(3H, m),
8.04(1H, s) 209 .delta. 0.93(3H, t, J=7.3Hz), 1.61-1.70(2H, m),
2.71(2H, t, J=7.3Hz), 4.85(2H, s), 7.10(1H, br-s), 7.48-7.53(2H,
m), 7.63(1H, s), 7.67-7.70(2H, m), 7.74(1H, d, J=2.0Hz), 8.05(1H,
s) 210 .delta. 0.90(3H, t, J=7.3Hz), 1.28-1.38(2H, m),
1.56-1.64(2H, m), 2.73(2H, t, J=7.8Hz), 4.85(2H, s), 7.06(1H,
br-s), 7.49-7.53(2H, m), 7.60(1H, s), 7.67-7.74(3H, m), 8.04(1H, s)
211 .delta.3.93(3H, s), 4.86(2H, s), 7.13(1H, br s), 7.53(1H, t,
J=8Hz), 7.61-7.65(2H, m), 7.71(1H, d, J=8Hz), 8.04(1H, s), 8.48(1H,
d, J=1.2Hz), 8.58(1H, s) 212 .delta. 2.47(3H, s), 4.85(2H, s),
7.08(1H, br-s), 7.40(1H, s), 7.51(1H, t, J=7.8Hz), 7.63(1H, s),
7.67-7.71(3H, m), 8.03(1H, s) 213 .delta.4.86(2H, s), 7.06(1H,
br.), 7.52(1H, t, J=7.8Hz), 7.67-7.71(3H, m), 7.67(2H, s), 8.05(1H,
s) 214 .delta. 2.26(3H, s), 2.45(3H, d, J=6.4Hz), 4.86(2H, s),
7.08(1H, br- s), 7.49-7.53(2H, m), 7.69-7.75(3H, m), 8.05(1H, br-s)
215 .delta. 2.35(3H, s), 2.58(3H, d, J=6.6Hz), 4.85(2H, s),
7.08(1H, br- s), 7.35(1H, s), 7.51(1H, t, J=8.1Hz), 7.68(2H, d,
J=8.1Hz), 7.73(1H, s), 8.04(1H, s) 216 .delta. 2.50(3H, s),
4.77(2H, br-s), 4.86(2H, s), 7.12(1H, br-s), 7.51-7.56(2H, m),
7.69(2H, d, J=7.3Hz), 8.84(1H, s), 8.08(1H, br-s) 217 .delta.
2.43(3H, s), 4.86(2H, s), 7.12(1H, br-s), 7.51(1H, t, J=7.9Hz),
7.57(1H, br-s), 7.69(1H, d, J=7.9Hz), 7.76(1H, br-s), 7.86(1H,
br-s), 8.08(1H, br-s) 218 .delta. 2.51(3H, s), 4.86(2H, s),
7.00(1H, br-s), 7.50-7.55(2H, m), 7.68-7.70(2H, m), 7.87(1H, br-s),
8.08(1H, br-s) 219 .delta. 2.62(3H, s), 4.86(2H, s), 7.00(1H,
br-s), 7.47(1H, s), 7.52(1H, t, J=7.8Hz), 7.68-7.70(2H, m),
7.89(1H, br-s), 8.07(1H, br- s) 220 .delta. 2.12(3H, s), 4.50(2H,
br-s), 4.86(2H, s), 7.14(1H, br-s), 7.29(1H, br-s), 7.51(1H, t,
J=7.8Hz), 7.68-7.70(2H, m), 7.77(1H, br- s), 8.04(1H, br-s) 221
.delta. 0.90(3H, t, J=7.3Hz), 1.28-1.37(2H, m), 1.55-1.63(2H, m),
2.48-2.60(2H, m), 2.73(2H, t, J=7.8Hz), 4.43(2H, t, J=6.3Hz),
6.85(1H, s), 7.46-7.50(2H, m), 7.60-7.68(3H, m), 7.73(1H, d,
J=1.5Hz), 8.00(1H, s) 222 .delta.1.32(6H, d, J=6.3Hz), 2.39(3H, s),
5.04(1H, septet, J=6.3Hz), 6.71(1H, s), 7.43-7.47(2H, m),
7.57-7.64(3H, m), 7.73(1H, s), 8.04(1H, s) 223 .delta. 1.32(6H, d,
J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H, t, J=8.1Hz),
7.63-7.68(1H, m), 7.67(2H, s), 7.75(1H, d, J=7.6Hz), 8.00(1H, s),
8.06(1H, t, J=1.7Hz), 8.93(1H, s) 224 (DMSO-d.sub.6).delta.
1.31(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H, t,
J=8.1Hz), 7.64(1H, d, J=8.1Hz), 7.79(1H, d, J=8.1Hz), 7.93(1H, s),
8.00(1H, s), 8.15(1H, 5), 8.26(1H, s), 9.36(1H, s) 225 .delta.
1.31(6H, d, J=6.3Hz), 2.34(6H, s), 5.03(1H, septet, J=6.3Hz),
6.73(1H, s), 7.33(2H, s), 7.44(1H, t, J=7.8Hz), 7.53-7.62(3H, m),
8.05(1H, s) 226 .delta. 1.31(6H, d, J=6.3Hz), 2.33(6H, s), 5.02(1H,
septet, J=6.3Hz), 6.75(1H, s), 7.33(2H, s), 7.43(1H, t, J=7.8Hz),
7.52-7.61(3H, m), 8.04(1H, s) 227 .delta. 4.84(2H, s), 7.24(1H, s),
7.45(1H, t, J=7.8Hz), 7.59-7.62(4H, m), 7.77(2H, d, J=8.8Hz),
7.99(1H, s), 8.16(1H, s) 228 .delta. 2.39(3H, s), 4.85(2H, s),
7.11(1H, br-s), 7.47-7.52(2H, m), 7.58(1H, s), 7.67-7.70(2H, m),
7.73(1H, s), 8.06(1H, s) 229 (DMSO-d.sub.6).delta. 4.86(2H, s),
7.45(1H, t, J=7.8Hz), 7.72(1H, s), 7.73(1H, d, J=7.8Hz),
7.83-7.84(2H, m), 8.14(1H, s), 9.27(1H, s), 9.34(1H, s) 230
(DMSO-d.sub.6).delta. 4.86(2H, s), 7.44(1H, t, J=8.1Hz), 7.67(1H,
s), 7.68(1H, s), 7.71-7.74(1H, m), 7.85(1H, d, J=7.3Hz), 8.15(1H,
s), 9.31(1H, s), 9.41(1H, br-s) 231 (DMSO-d.sub.6).delta. 4.96(2H,
s), 7.51(1H, t, J=7.8Hz), 7.65-7.73(2H, m), 8.13(1H, s), 8.15(1H,
s), 8.49(1H, s), 10.41(1H, s), 10.58(1H, s) 232
(DMSO-d.sub.6).delta. 4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.70(1H,
d, J=7.8Hz), 7.88(1H, d, J=7.8Hz), 7.94(1H, s), 8.08(1H, s),
8.16(1H, s), 9.33(1H, s), 9.42(1H, s) 233 .delta. 2.34(6H, s),
4.85(2H, s), 7.10(1H, br), 7.34(2H, s), 7.47-7.51(2H, m),
7.65-7.68(2H, m), 8.06(1H, s) 234 .delta. 2.34(6H, s), 4.85(2H, s),
7.10(1H, br), 7.35(2H, s), 7.47-7.52(2H, m), 7.65-7.68(2H, m),
8.05(1H, s) 235 .delta. 4.84(2H, s), 7.17(1H, br-s), 7.49(1H, t,
J=7.8Hz), 7.63(1H, d, J=7.8Hz), 7.67(1H, d, J=7.8Hz), 7.94(1H, s),
8.07(1H, s) 236 .delta. 4.85(2H, s), 7.14(1H, s), 7.51(1H, t,
J=7.8Hz), 7.68-7.73(2H, m), 7.83(1H, s), 7.86(2H, s), 8.07(1H, s)
237 .delta. 2.48-2.60(2H, m), 4.43(2H, t, J=6.3Hz), 6.90(1H, s),
7.48(1H, t, J=7.8Hz), 7.63-7.69(2H, m), 7.86(3H, s), 8.03(1H, s)
238 (DMSO-d.sub.6).delta. 2.50-2.61(2H, m), 4.41(2H, t, J=6.3Hz),
7.43(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.71(1H, s),
7.80-7.84(2H, m), 8.06(1H, s), 8.82(1H, s), 9.26(1H, s) 239 .delta.
1.34(3H, t, J=7.3Hz), 4.26(2H, q, J=7.3Hz), 6.77(1H, br-s),
7.46-7.53(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-7.94(3H, m),
8.39(1H, s), 8.71(1H, d, J=8.8Hz) 240 .delta. 1.32(6H, d, J=6.3Hz),
5.06(1H, septet, J=6.3Hz), 6.74(1H, s), 7.45-7.52(2H, m), 7.70(1H,
d, J=7.3Hz), 7.86-7.94(3H, m), 8.40(1H, s), 8.71(1H, d, J=8.8Hz)
241 .delta. 4.58(1H, dd, J=2.0Hz, 5.8Hz), 4.85(1H, dd, J=2.0Hz,
4.2Hz), 7.06(1H, br-s), 7.30(1H, d, J=6.4Hz), 7.49-7.57(2H, m),
7.74(1H, d, J=7.8Hz), 7.87(1H, d, J=7.8Hz), 7.91(1H, s), 7.99(1H,
s), 8.40(1H, s), 8.71(1H, d, J=8.8Hz) 242 .delta.1.62-1.70(2H, m),
1.71-1.87(4H, m), 1.89-1.96(2H, m), 5.22-5.26(1H, m), 6.72(1H, s),
7.45-7.51(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-7.93(3H, m),
8.34(1H, s), 8.70(1H, d, J=8.8Hz) 243 .delta. 3.76(2H, t, J=5.4Hz),
4.47(2H, t, J=5.4Hz), 6.97(1H, br-s), 7.47-7.56(2H, m), 7.69(1H, d,
J=7.8Hz), 7.86-7.91(2H, m), 7.97(1H, s), 8.39(1H, s), 8.71(1H, d,
J=8.8Hz) 244 .delta. 2.82(2H, t, J=6.3Hz), 4.41(2H, t, J=6.3Hz),
7.46(1H, t, J=7.8Hz), 7.54-7.57(1H, m), 7.81(1H, d, J=8.3Hz),
7.88(1H, d, J=8.8Hz), 7.91(1H, s), 8.10(1H, s), 8.56-8.63(2H, m),
9.55(1H, br-s) 245 .delta.4.40(2H, dt, J=3.9Hz, 14.1Hz), 6.04(1H,
tt, J=3.9Hz, 55.3Hz), 7.43-7.48(1H, m), 7.55(1H, d, J=7.8Hz),
7.80(1H, d, J=7.3Hz), 7.86(1H, d, J=8.8Hz), 7.91(1H, s), 8.07(1H,
s), 8.53(1H, s), 8.64(1H, d, J=8.8Hz), 9.42(1H, s) 246
.delta.4.56(2H, d, J=5.9Hz), 5.92(1H, t, J=5.9Hz), 6.97(1H, br-s),
7.49-7.57(2H, m), 7.69(1H, d, J=7.3Hz), 7.87-7.92(2H, m), 7.98(1H,
s), 8.39(1H, s), 8.71(1H, d, J=8.8Hz) 247 .delta. 4.86(2H, s),
7.15(1H, br-s), 7.50-7.59(2H, m), 7.72(1H, d, J=7.8Hz),
7.86-7.92(2H, m), 8.02(1H, s), 8.40(1H, s), 8.71(1H, d, J=8.8Hz)
248 .delta.5.05(2H, s), 7.09(1H, br-s), 7.51-7.59(2H, m), 7.73(1H,
d, J=7.8Hz), 7.88(1H, d, J=8.3Hz), 7.92(1H, s), 8.03(1H, s),
8.39(1H, s), 8.72(1H, d, J=8.8Hz) 249 .delta. 2.49-2.60(2H, m),
4.44(2H, t, J=6.3Hz), 6.86(1H, br-s), 7.48-7.56(2H, m), 7.69(1H, d,
J=6.3Hz), 7.88(1H, d, J=8.8Hz), 7.92(1H, s), 7.96(1H, s), 8.39(1H,
s), 8.71(1H, d, J=8.8Hz) 250 .delta.4.68(2H, t, J=13.2Hz), 708(1H,
br-s), 7.50-7.59(2H, m), 7.70(1H, br-d, J=7.3Hz), 7.87-7.92(2H, m),
8.00(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.7Hz) 251 .delta.5.29(2H,
s), 6.92(1H, br-s), 7.47-7.55(4H, m), 7.65-7.70(3H, m), 7.87(1H, d,
J=8.8Hz), 7.92(1H, s), 7.97(1H, s), 8.38(1H, br-s), 8.71(1H, d,
J=8.8Hz) 252 .delta.5.23(2H, s), 6.82(1H, br-s), 7.37(1H, d,
J=8.3Hz), 7.50-7.53(2H, m), 7.6(1H, m), 7.75(1H, dd, J=2.4Hz,
8.3Hz), 7.87-7.96(3H, m), 8.38(1H, br-s), 8.47(1H, d, J=2.4Hz),
8.72(1H, d, J=8.3Hz) 253 .delta. 1.31(6H, d, J=6.3Hz), 2.33(6H, s),
5.02(1H, septet, J=6.3Hz), 6.75(1H, br-s), 7.33(2H, s), 7.43(1H, t,
J=7.8Hz), 7.54-7.61(3H, m), 8.04(1H, s) 254 .delta. 2.34(6H, s),
4.39(2H, dt, J=3.9Hz, 13.6Hz), 6.01(1H, tt, J=3.9Hz, 54.6Hz),
6.98(1H, s), 7.34(2H, s), 7.46-7.50(2H, m), 7.60-7.66(2H, m),
8.02(1H, s) 255 .delta. 2.34(6H, s), 4.61-4.66(2H, m),
4.71-4.77(2H, m), 5.18-5.30(1H, m), 7.12(1H, s), 7.34(2H, s),
7.45-7.50(1H, m), 7.52-7.66(2H, m), 7.76-7.84(1H, m), 8.04(1H, s)
256 .delta. 2.34(6H, s), 4.58(2H, q, J=8.3Hz), 7.02(1H, s),
7.34(2H, s), 7.45-7.51(2H, m), 7.62-7.67(2H, m), 8.02(1H, s) 257
.delta. 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.34(2H, s),
7.47-7.51(2H, m), 7.63-7.67(2H, m), 8.05(1H, s) 258 .delta.1.48(3H,
d, J=6.8Hz), 2.34(6H, s), 5.30-5.36(1H, m), 6.95(1H, br- s),
7.30(2H, s), 7.46-7.51(2H, m), 7.60-7.67(2H, m), 8.03(1H, br-s) 259
.delta. 2.35(6H, s), 2.49-2.59(2H, m), 4.42(2H, t, J=6.3Hz),
6.85(1H, br- s), 7.34(2H, s), 7.45-7.49(2H, m), 7.60-7.65(2H, m),
8.02(1H, br-s) 300 .delta. 4.85(2H, s), 7.10(1H, br), 7.50(1H, t,
J=7.8Hz), 7.68-7.71(3H, m), 7.72(2H, s), 8.04(1H, s) 301 .delta.
4.85(2H, s), 7.08(1H, br), 7.51-7.55(1H, m), 7.69-7.72(2H, m),
7.84(1H, s), 8.06(2H, s), 8.10(1H, s) 331 .delta. 2.29(6H, s),
4.85(2H, s), 7.11-7.19(3H, m), 7.39(1H, s), 7.49(1H, t, J=7.9Hz),
7.66-7.73(2H, m), 8.00(1H, s) 348 .delta. 2.35(6H, s), 3.81(3H, s),
6.80(1H, br), 7.36(2H, s), 7.44-7.63(4H, m), 8.02(1H, s) 377
.delta. 2.36(6H, s), 4.85(2H, s), 7.09(1H, s), 7.37(2H, s),
7.44(1H, s), 7.50(1H, t, J=8.3Hz), 7.67(2H, d, J=7.3Hz), 8.05(1H,
s) 424 .delta.4.85(2H, s), 7.10(1H, s), 7.51(1H, t, J=7.8Hz),
7.69-7.70(3H, m), 7.73(2H, s), 8.05(1H, s) 464 .delta.
2.47-2.59(2H, m), 4.41(2H, t, J=6.3Hz), 6.96(1H, br-s), 7.46(1H, t,
J=7.8Hz), 7.63-7.67(2H, m), 7.83(1H, s), 7.91(2H, s), 8.00(1H, s)
471 .delta. 4.85(2H, s), 7.13(1H, br-s), 7.50(1H, t, J=7.8Hz),
7.68-7.74(3H, m), 7.92(2H, s), 8.04(1H, s) 511
(DMSO-d.sub.6).delta. 2.67-2.78(2H, m), 4.34(2H, t, J=5.9Hz),
7.50(1H, t, J=7.8Hz), 7.68-7.73(2H, m), 8.13(1H, s), 8.52(2H, s),
10.02(1H, s), 10.77(1H, s) 518 (DMSO-d.sub.6).delta. 4.96(2H, s),
7.52(1H, t, J=7.8Hz), 7.71-7.75(2H, m), 8.16(1H, s), 8.51(2H, s),
10.42(1H, s), 10.79(1H, s) 565 .delta.4.86(2H, s), 7.00(1H, br-s),
7.52(1H, t, J=8.3Hz), 7.70-7.73(3H, m), 7.93(2H, s), 8.06(1H, s)
605 .delta. 2.49-2.60(2H, m), 4.43(2H, t, J=6.3Hz), 6.82(1H, s),
7.49(1H, t, J=7.8Hz), 7.66-7.68(3H, m), 7.94(2H, s), 8.01(1H, s)
612 .delta.4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.72(1H, d, J=7.8Hz),
7.94(1H, br-s), 7.93(2H, s), 8.13(1H, s), 9.02(1H, s), 9.17(1H, s)
659 .delta.4.86(2H, s), 7.06(1H, s), 7.51(1H, t, J=7.8Hz),
7.68-7.71(3H, m),
7.93(2H, s), 8.06(1H, s) 706 .delta.4.84(2H, s), 7.40(1H, br-s),
7.48(1H, t, J=7.8Hz), 7.67-7.75(2H, m), 8.00(1H, s), 8.09(2H, s),
8.24(1H, s) 770 .delta. 2.39(3H, s), 4.86(2H, s), 7.00(1H, br-s),
7.48-7.67(5H, m), 7.79(1H, s), 8.04(1H, s), 8.24(1H, d, J=8.8Hz)
800 .delta. 2.31(6H, s), 4.85(2H, s), 7.11(1H, br-s), 7.43(2H, s),
7.47-7.53(2H, m), 7.66(1H, s), 7.67(1H, s), 8.05(1H, s) 817
.delta.0.89(3H, t, J=7.3Hz), 1.24-1.37(2H, m), 1.55-1.63(2H, m),
2.47-2.59(2H, m), 2.70(2H, t, J=7.8Hz), 4.42(2H, t, J=5.9Hz),
6.96(1H, br-s), 7.43-7.47(2H, m), 7.57(1H, d, J=1.5Hz),
7.62-7.64(2H, m), 7.74(1H, s), 8.00(1H, s) 818 .delta.0.86(3H, t,
J=7.3Hz), 1.24-1.33(2H, m), 1.49-1.57(2H, m), 2.45-2.56(2H, m),
2.67(2H, t, J=7.8Hz), 4.38(2H, t, J=6.3Hz), 7.15(1H, s), 7.39(1H,
t, J=7.8Hz), 7.48(1H, s), 7.62-7.64(2H, m), 7.88(1H, s), 7.93(1H,
d, J=2.0Hz), 8.01(1H, s) 819 .delta. 0.81(3H, t, J=7.3Hz), 1.25(3H,
d, J=6.8Hz), 1.53-1.64(2H, m), 2.49-2.60(2H, m), 2.92-3.01(1H, m),
4.43(2H, t, J=5.9Hz), 6.87(1H, br), 7.46-7.51(2H, m), 7.62-7.67(3H,
m), 7.74(1H, d, J=1.5Hz), 8.01(1H, s) 820 .delta.1.32(6H, d,
J=6.3Hz), 2.36(3H, s), 5.01-5.07(1H, m), 6.69(1H, s), 7.11-7.13(2H,
m), 7.44(1H, t, J=8.3Hz), 7.55-7.59(2H, m), 7.68(1H, br-s),
7.95(1H, d, J=8.3Hz), 7.99(1H, s) 821 .delta. 1.27(6H, d, J=6.8Hz),
1.31(6H, d, J=6.3Hz), 2.96(1H, septet, J=6.8Hz), 5.05(1H, septet,
J=6.3Hz), 6.79(1H, s), 7.42-7.52(4H, m), 7.72(1H, d, J=7.8Hz),
7.86(1H, t, J=2.0Hz), 8.14(1H, s), 8.21(1H, d, J=8.3Hz) 822 .delta.
1.33(6H, d, J=6.6Hz), 5.01-5.09(1H, m), 6.73(1H, s), 7.41-7.52(2H,
m), 7.57-7.60(1H, m), 7.65(1H, s), 8.05(1H, s), 8.20(2H, s),
8.35(1H, s) 823 .delta. 1.32(6H, d, J=6.3Hz), 5.04(1H, septet,
J=6.3Hz), 6.70(1H, br-s), 6.98-7.06(1H, m), 7.45(1H, t, J=7.8Hz),
7.53-7.55(1H, m), 7.62(1H, d, J=8.8Hz), 7.94(2H, s), 8.07-8.14(1H,
m) 824 .delta.1.32(6H, d, J=6.1Hz), 2.46(3H, s), 2.54(3H, d,
J=15Hz), 5.04(1H, septet, J=6.1Hz), 6.72(1H, s), 7.40-7.44(2H, m),
7.51-7.56(3H, m), 7.94(1H, s), 7.97(1H, s) 825 .delta. 1.31(6H, d,
J=6.3Hz), 2.30(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s),
7.20(1H, d, J=2.2Hz), 7.32(1H, d, J=2.2Hz), 7.43(1H, t, J=7.8Hz),
7.59-7.62(3H, m), 8.00(1H, s) 826 .delta.1.31(6H, d, J=6.3Hz),
2.28(3H, s), 2.31(3H, s), 5.03(1H, septet, J=6.3Hz), 6.71(1H,
br-s), 7.01(1H, s), 7.13(1H, s), 7.43(1H, t, J=7.8Hz),
7.61-7.63(3H, m), 7.97(1H, s) 827 .delta. 1.31(6H, d, J=6.1Hz),
2.25(6H, s), 5.03(1H, septet, J=6.1Hz), 6.70(1H, br- s), 7.26(2H,
s), 7.38(1H, br-s), 7.43(1H, t, J=7.8Hz), 7.55-7.61(2H, m),
8.01(1H, s) 828 .delta. 1.31(6H, d, J=6.3Hz), 2.24(6H, s), 5.02(1H,
septet, J=6.3Hz), 6.71(1H, br- s), 7.26(2H, s), 7.39-7.44(2H, m),
7.55-7.60(2H, m), 8.00(1H, s) 829 .delta.1.31(6H, d, J=6.4Hz),
2.23(6H, s), 5.03(1H, septet, J=6.4Hz), 6.69(1H, br-s), 7.37(1H,
br-s), 7.43(1H, t, J=7.8Hz), 7.48(2H, s), 7.55-7.61(2H, m),
8.01(1H, br-s) 830 .delta.1.32(6H, d, J=6.3Hz), 2.35(6H, s),
5.04(1H, septet, J=6.3Hz), 6.72(1H, s), 7.32-7.36(3H, m),
7.41-7.46(4H, m), 7.56-7.63(4H, m), 8.00(1H, s) 831 .delta.1.32(6H,
d, J=6Hz), 2.30(3H, s), 2.32(6H, s), 5.04(1H, septet, J=6Hz),
6.73(1H, s), 7.08(2H, s), 7.22-7.26(4H, m), 7.43-7.48(2H, m),
7.61-7.63(2H, m), 8.01(1H, s) 832 .delta.1.32(6H, d, J=6Hz),
2.31(6H, s), 2.42(3H, s), 5.04(1H, septet, J=6Hz), 6.71(1H, s),
7.16(1H, d, J=8Hz), 7.30-7.59(7H, m), 7.62(2H, t, J=8Hz), 8.01(1H,
s) 833 .delta.1.31(6H, d, J=6Hz), 2.33(6H, s), 2.49(3H, s),
5.03(1H, septet, J=6Hz), 6.73(1H, s), 7.12-7.25(2H, m), 7.32(2H,
s), 7.42-7.52(4H, m), 7.59-7.63(2H, m), 7.99(1H, s) 834
.delta.1.32(6H, d, J=6Hz), 2.32(6H, s), 3.80(3H, s), 5.04(1H,
septet, J=6Hz), 6.73(1H, s), 6.97(1H, d, J=8Hz), 7.02(1H, t,
J=7Hz), 7.27(2H, s), 7.30(2H, d, J=7Hz), 7.34-7.46(2H, m),
7.60-7.63(2H, m), 7.95(1H, s) 835 .delta.1.32(6H, d, J=7Hz),
2.34(6H, s), 3.87(3H, s), 5.04(1H, septet, J=7Hz), 6.72(1H, s),
6.88-6.91(1H, m), 7.11(1H, t, J=2Hz), 7.16(1H, td, J=8Hz, 1Hz),
7.33-7.37(3H, m), 7.43-7.50(2H, m), 7.59-7.64(2H, m), 8.01(1H, s)
836 .delta.1.32(6H, d, J=7Hz), 2.33(6H, s), 3.85(3H, s), 5.04(1H,
septet, J=7Hz), 6.73(1H, br-s), 6.96(2H, d, J=9Hz), 7.29(2H, s),
7.42-7.52(4H, m), 7.60-7.63(2H, m), 8.00(1H, s) 837 .delta.1.32(6H,
d, J=6Hz), 1.44(3H, t, J=7Hz), 2.33(6H, s), 4.08(2H, q, J=7Hz),
5.04(1H, septet, J=6Hz), 6.72(1H, s), 6.94-6.97(2H, m), 7.29(2H,
s), 7.42-7.52(4H, m), 7.61-7.63(2H, m), 7.99(1H, s) 838
.delta.1.31(6H, d, J=6Hz), 2.34(6H, s), 2.53(3H, s), 5.04(1H,
septet, J=6Hz), 6.72(1H, s), 7.31-7.65(10H, m), 8.00(1H, s). 839
.delta.1.31(6H, d, J=6.3Hz), 2.34(6H, s), 5.04(1H, septet,
J=6.3Hz), 6.72(1H, s), 7.12-7.32(5H, m), 7.41-7.48(3H, m),
7.61-7.63(2H, m), 7.99(1H, s) 840 .delta.1.32(6H, d, J=7Hz),
2.34(6H, s), 5.03(1H, septet, J=7Hz), 6.74(1H, br s), 7.01-7.05(1H,
m), 7.28-7.64(9H, m), 8.02(1H, s) 841 .delta.1.31(6H, d, J=7Hz),
2.34(6H, s), 5.04(1H, septet, J=7Hz), 6.73(1H, s), 7.11(2H, t,
J=9Hz), 7.28(2H, s), 7.42-7.63(6H, m), 8.01(1H, s) 842
.delta.1.24(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.32(3H, s),
2.86(1H, septet, J=6.8Hz), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s),
7.08(1H, s), 7.33(1H, d, J=2.0Hz), 7.43(1H, t, J=7.8Hz),
7.61-7.65(3H, m), 7.96(1H, s) 843 .delta.1.32(6H, d, J=6.3Hz),
2.37(3H, s), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.46(1H, t,
J=7.8Hz), 7.51-7.57(2H, m), 7.61-7.65(2H, m), 7.90(1H, s), 8.08(1H,
s) 844 .delta. 1.32(6H, d, J=6.3Hz), 2.35(3H, s), 5.03(1H, septet,
J=6.3Hz), 6.72(1H, s), 7.09(1H, s), 7.21(1H, d, J=2.2Hz), 7.44(1H,
t, J=8.1Hz), 7.52-7.61(3H, m), 8.02(1H, s) 845 .delta. 1.29(6H, d,
J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.98(1H, septet, J=6.8Hz), 5.04(1H,
septet, J=6.3Hz), 6.70(1H, s), 7.42-7.48(2H, m), 7.56-7.67(4H, m),
7.92(1H, s) 846 .delta. 1.32(6H, d, J=6.3Hz), 5.03(1H, septet,
J=6.3Hz), 6.75(1H, br-s), 7.41-7.51(2H, m), 7.62-7.65(1H, m),
7.91(1H, br-s), 8.08(1H, s) 847 (DMSO-d.sub.6).delta. 1.24-1.44(5H,
m), 1.68-1.80(5H, m), 2.46-2.50(1H, m), 4.97(2H, s), 7.19(2H, d,
J=8.8Hz), 7.47(1H, t, J=7.8Hz), 7.60-7.70(4H, m), 8.04(1H, s),
10.19(1H, s), 10.37(1H, s) 848 .delta. 4.84(2H, s), 7.29(1H, d,
J=7.8Hz), 7.35(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.56-7.67(3H, m),
7.75(1H, d, J=7.3Hz), 7.97(1H, s), 8.23(1H, s), 8.37(1H, d,
J=7.8Hz) 849 .delta. 4.85(2H, s), 7.12(1H, br-s), 7.47(1H, t,
J=7.8Hz), 7.59-7.67(4H, m), 7.72-7.75(2H, m), 7.99(1H, s), 8.03(1H,
s) 850 (DMSO-d.sub.6).delta. 4.87(2H, s), 7.43(1H, t, J=7.8Hz),
7.65(1H, d, J=7.8Hz), 7.82(1H, d, J=7.8Hz), 7.96(2H, d, J=8.8Hz),
8.07(1H, s), 8.18-8.22(2H, m), 9.66(1H, br), 10.51(1H, s) 851
.delta.4.85(2H, s), 6.67(1H, br-s), 7.47(1H, t, J=7.8Hz),
7.60-7.64(2H, m), 7.65(2H, d, J=8.8Hz), 7.74(2H, d, J=8.8Hz),
7.98(1H, s), 8.00(1H, s) 852 .delta.4.86(2H, s), 7.09(1H, br-s),
7.48-7.53(1H, m), 7.61-7.65(2H, m), 7.81(2H, d, J=8.8Hz), 7.95(2H,
d, J=8.8Hz), 7.95-8.04(1H, m), 8.14(1H, s) 854 .delta.0.90(3H, t,
J=7.3Hz), 1.28-1.38(2H, m), 1.56-1.65(2H, m), 2.72(2H, t, J=7.8Hz),
4.85(2H, s), 7.14(1H, br-s), 7.45(1H, s), 7.50(1H, t, J=7.8Hz),
7.58(1H, d, J=1.5Hz), 7.66-7.68(3H, m), 8.04(1H, s) 855 .delta.
0.88(3H, t, J=7.3Hz), 1.24-1.35(2H, m), 1.52-1.60(2H, m), 2.70(2H,
t, J=7.8Hz), 4.84(2H, s), 7.27(1H, s), 7.46-7.50(2H, m),
7.67-7.69(2H, m), 7.76(1H, s), 7.94(1H, d, J=1.5Hz), 8.06(1H, s)
856 .delta. 0.81(3H, t, J=7.3Hz), 1.25(3H, d, J=5.9Hz),
1.55-1.65(2H, m), 2.91-3.01(1H, m), 4.85(2H, s), 7.14(1H, br),
7.50-7.53(2H, m), 7.61-7.77(4H, m), 8.05(1H, s) 857 .delta.0.90(3H,
t, J=7.3Hz), 1.31(3H, d, J=6.8Hz), 1.63-1.74(2H, m), 2.82-2.91(1H,
m), 4.85(2H, s), 7.22(1H, s), 7.47-7.53(3H, m), 7.58-7.62(1H, m),
7.66(1H, d, J=8.3Hz), 7.93(1H, s), 8.05(1H, s), 8.13-8.15(1H, m)
858 .delta. 2.36(3H, s), 4.85(2H, s), 7.11-7.14(3H, m), 7.49(1H, t,
J=8.3Hz), 7.61-7.69(3H, m), 7.95(1H, d, J=8.3Hz), 8.02(1H, s) 859
.delta. 2.31(3H, s), 4.34(2H, q, J=7.8Hz), 4.84(2H, s),
6.80-6.86(2H, m), 7.16(1H, br-s), 7.47(1H, t, J=7.8Hz),
7.60-7.72(4H, m), 7.99(1H, br-s) 860 .delta. 2.39(3H, s), 4.85(2H,
s), 7.09-8.14(9H, m) 861 .delta. 2.31(3H, s), 4.84(2H, s), 7.17(1H,
br), 7.20-7.23(2H, m), 7.47(1H, t, J=8.1), 7.58-7.67(3H, m),
7.84-7.87(1H, m), 8.00(1H, s) 862 .delta. 1.27(6H, d, J=6.8Hz),
2.97(1H, septet, J=6.8Hz), 4.85(2H, s), 7.18(1H, br), 7.46-7.51(3H,
m), 7.57(1H, dd, J=1.5Hz, 7.8Hz), 7.74(1H, d, J=7.8Hz), 7.94(1H,
s), 8.14(1H, s), 8.21(1H, d, J=8.3Hz) 863 .delta.4.87(2H, s),
7.51-8.01(8H, m), 8.86(1H, s) 864 .delta. 4.87(2H, s), 7.08(1H,
br.), 7.49-7.58(4H, m), 8.07(1H, br.), 8.20(3H, s) 865 .delta.
4.86(2H, s), 7.08(1H, br-s), 7.48-7.60(3H, m), 7.64(1H, d,
J=2.4Hz), 7.72(1H, d, J=7.3Hz), 7.98(1H, s), 8.18(1H, s), 8.39(1H,
d, J=8.8Hz) 866 .delta. 4.85(2H, s), 7.06(1H, br), 7.41-7.51(2H,
m), 7.60(1H, s), 7.65-7.74(4H, m), 7.97(1H, s) 867 .delta.4.86(2H,
s), 7.10(1H, br-s), 7.48-7.57(2H, m), 7.71(1H, d, J=8.3Hz),
7.90-7.97(3H, m), 8.19(1H, br-s), 8.22(1H, d, J=8.8Hz) 868 .delta.
4.85(2H, s), 7.12(1H, br-s), 7.46-7.56(4H, m), 7.71(1H, d,
J=7.8Hz), 7.99(1H, s), 8.14(1H, s), 8.48(1H, d, J=8.8Hz) 869
.delta. 4.84(2H, s), 6.97-7.05(1H, m), 7.22(1H, br-s), 7.48(1H, t,
J=7.8Hz), 7.59(1H, d, J=7.8Hz), 7.69(1H, d, J=7.8Hz), 7.96(1H, s),
7.98(1H, s), 8.05-8.12(1H, m) 870 .delta. 2.46(3H, s), 2.55(3H, d,
J=14Hz), 4.86(2H, s), 7.13(1H, br s), 7.40(1H, s), 7.46-7.62(4H,
m), 7.88(1H, s), 7.99(1H, s) 871 .delta. 2.34(3H, s), 2.38(3H, s),
4.85(2H, s), 6.97-8.03(8H, m) 872 .delta. 2.31(6H, s), 3.99(1H, s),
4.85(2H, s), 7.15(1H, br-s), 7.45-7.51(4H, m), 7.64-7.66(2H, m),
8.01(1H, s) 873 .delta. 2.34(6H, s), 3.74(1H, s), 4.85(2H, s),
7.08(1H, br-s), 7.48(1H, s), 7.49(2H, s), 7.52(1H, s),
7.65-7.67(2H, m), 8.04(1H, s) 874 .delta. 2.30(6H, s), 4.87(2H, s),
7.08(1H, br), 7.49-7.58(4H, m), 8.07(1H, br), 8.20(3H, s) 875
.delta. 2.25(6H, s), 4.85(2H, s), 7.07(1H, br), 7.12(2H, s),
7.36(1H, br- s), 7.48(1H, t, J=7.8Hz), 7.64-7.66(2H, m), 8.02(1H,
s) 876 .delta. 2.28(3H, s), 2.31(3H, s), 4.84(2H, s), 7.00(1H, s),
7.12(1H, s), 7.18(1H, br), 7.47(1H, t, J=7.8Hz), 7.60(1H, s),
7.66-7.68(2H, m), 7.99(1H, s) 877 .delta. 2.19(6H, s), 4.82(2H, s),
7.22(2H, s), 7.41(1H, t, J=8.1Hz), 7.48(1H, br), 7.61-7.66(3H, m),
7.99(1H, s) 878 .delta. 2.22(6H, s), 4.84(2H, s), 7.13(1H, br-s),
7.39(1H, s), 7.45-7.49(3H, m), 7.64-7.65(2H, m), 8.01(1H, br-s) 879
.delta. 2.35(6H, s), 4.85(2H, s), 7.09(1H, s), 7.32-7.69(11H, m),
8.02(1H, s) 880 .delta. 2.30(3H, s), 2.32(6H, s), 4.85(2H, s),
7.09(2H, s), 7.13(1H, s), 7.21-7.27(4H, m), 7.46-7.51(2H, m),
7.68(2H, d, J=7Hz), 8.03(1H, s) 881 .delta. 2.34(6H, s), 2.42(3H,
s), 4.85(2H, s), 7.12-7.23(2H, m), 7.29-7.39(4H, m), 7.47-7.52(2H,
m), 7.68(2H, d, J=7Hz), 8.03(1H, s) 882 .delta. 2.34(6H, s),
2.40(3H, s), 4.85(2H, s), 7.13(1H, d, J=4Hz), 7.23-7.26(2H, m),
7.30(2H, s), 7.33-7.50(4H, m), 7.67(2H, d, J=8Hz), 8.02(1H, s) 883
.delta. 2.32(6H, s), 3.81(3H, s), 4.85(2H, s), 6.97-7.04(2H, m),
7.10(1H, br s), 7.28(2H, s), 7.30-7.34(2H, m), 7.42(1H, s),
7.49(1H, t, J=8Hz), 7.66-7.70(2H, m), 7.99(1H, s) 884 .delta.
2.35(6H, s), 3.88(3H, s), 4.85(2H, s), 6.89-6.91(1H, m),
7.10-7.18(3H, m), 7.33-7.37(3H, m), 7.47-7.52(2H, m), 7.68(2H, d,
J=7Hz), 8.03(1H, s) 885 .delta. 2.33(6H, s), 3.86(3H, s), 4.85(2H,
s), 6.96(2H, d, J=9Hz), 7.14(1H, br s), 7.30(2H, s), 7.47-7.53(4H,
m), 7.68(2H, d, J=7Hz), 8.02(1H, s) 886 .delta.1.44(3H, t, J=7Hz),
2.33(6H, s), 4.08(2H, q, J=7Hz), 4.85(2H, s), 6.95(2H, d, J=9Hz),
7.13(1H, s), 7.30(2H, s), 7.45-7.52(4H, m), 7.68(2H, d, J=7Hz),
8.01(1H, s) 887 .delta. 2.33(6H, s), 2.53(3H, s), 4.84(2H, s),
7.14(1H, s), 7.30-7.38(4H, m), 7.46-7.57(4H, m), 7.67(2H, d,
J=6Hz), 8.02(1H, s) 888 .delta. 2.34(6H, s), 4.85(2H, s),
7.10-7.34(6H, m), 7.41-7.52(3H, m), 7.68(2H, d, J=8Hz), 8.02(1H, s)
889 .delta. 2.34(6H, s), 4.85(2H, s), 7.01-7.06(1H, m), 7.16(1H, br
s), 7.25-7.50(8H, m), 7.68(1H, d, J=8Hz), 8.03(1H, s) 890 .delta.
2.33(6H, s), 4.85(2H, s), 7.09-7.15(3H, m), 7.29(2H, s),
7.46-7.55(4H, m), 7.67-7.69(2H, m), 8.03(1H, s)
891 .delta. 2.34(6H, s), 4.85(2H, s), 7.09(1H, br s), 7.18-7.30(4H,
m), 7.34-7.51(3H, m), 7.67-7.69(2H, m), 8.04(1H, s) 892 .delta.
2.30(9H, s), 4.85(2H, s), 7.05(1H, t, J=8.8Hz), 7.14(1H, br s),
7.28(2H, s), 7.32-7.51(4H, m), 7.67-7.69(2H, m), 8.03(1H, s) 893
.delta. 2.31(6H, s), 4.85(2H, s), 6.69(1H, s), 7.09(1H, br-s),
7.25(2H, s), 7.41(1H, s), 7.47-7.51(2H, m), 7.66-7.68(2H, m),
7.72(1H, s), 8.02(1H, s) 894 .delta. 2.30(6H, s), 4.84(2H, s),
7.07-7.09(1H, m), 7.25(1H), 7.27-7.29(1H, m), 7.36(2H, s), 7.36(2H,
s), 7.45-7.50(2H, m), 7.65-7.67(2H, m), 8.02(1H, s) 895 .delta.
2.32(6H, s), 4.85(2H, s), 7.18(1H, s), 7.35-7.50(7H, m), 7.67(2H,
d, J=6.8Hz), 8.02(1H, s) 896 .delta. 2.31(3H, s), 4.85(2H, s),
7.10(1H, br), 7.20(1H, d, J=2.2Hz), 7.32(1H, d, J=2.2Hz), 7.49(1H,
t, J=7.8Hz), 7.57(1H, s), 7.66-7.68(2H, m), 8.02(1H, s) 897
(DMSO-d.sub.6).delta. 4.85(2H, s), 7.44(1H, t, J=7.8Hz),
7.63-7.68(2H, m), 7.72(1H, d, J=2.4Hz), 7.84(1H, s), 8.06(1H, s),
8.80(1H, s), 9.09(1H, s) 898 .delta.4.85(2H, s), 7.00(1H, br-s),
7.51(1H, t, J=8.3Hz), 7.69-7.72(5H, m), 8.05(1H, s) 899
.delta.4.86(2H, s), 7.00(1H, br-s), 7.53(1H, t, J=7.8Hz),
7.67-7.73(2H, m), 7.92(1H, s), 8.05(2H, s), 8.11(1H, s) 900
(DMSO-d.sub.6).delta. 4.98(2H, s), 7.52(1H, t, J=7.8Hz),
7.70-7.75(2H, m), 8.17(1H, s), 8.31(2H, s), 10.42(1H, s), 10.63(1H,
s) 901 (DMSO-d.sub.6).delta. 1.24-1.47(5H, m), 1.66-1.80(5H, m),
2.54-2.60(1H, m), 4.96(2H, s), 7.48(1H, t, J=7.8Hz), 7.60(2H, s),
7.67-7.71(2H, m), 8.11(1H, s), 10.24(1H, s), 10.37(1H, s) 902
(DMSO-d.sub.6).delta. 4.86(2H, s), 7.44(1H, t, J=7.8Hz), 7.67(1H,
d, J=7.8Hz), 7.82(1H, d, J=2.0Hz), 7.85(1H, s), 8.05(1H, d,
J=2.0Hz), 8.06(1H, d, J=7.8Hz), 9.04(1H, s), 9.27(1H, s) 903
.delta.4.86(2H, s), 7.00(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.70(2H,
d, J=7.8Hz), 7.75(1H, s), 7.94(2H, s), 8.06(1H, s) 904 .delta.
2.20(3H, s), 4.85(2H, s), 6.60(1H, d, J=2.4Hz), 7.17(1H, br.),
7.50(1H, t, J=7.8Hz), 7.54(1H, s), 7.59(1H, s), 7.69(1H, d,
J=7.8Hz), 7.72(1H, br), 8.03(1H, s) 905 .delta. 2.36(3H, s),
4.85(2H, s), 7.08(1H, br-s), 7.10(1H, s), 7.22-7.23(1H, m),
7.50(1H, t, J=8.1Hz), 7.59(1H, s), 7.67-7.69(2H, m), 8.04(1H, s)
906 .delta. 2.36(3H, s), 4.86(2H, s), 4.88(2H, s), 7.04(1H, br.),
7.12(1H, d, J=2.4Hz), 7.27(1H, s), 7.50(1H, t, J=7.8Hz), 7.56(1H,
s), 7.67-7.70(2H, m), 8.02(1H, s) 907 .delta. 2.38(3H, s), 4.85(2H,
s), 7.14(1H, br), 7.49-7.53(2H, m), 7.62-7.70(3H, m), 7.85(1H, s),
8.09(1H, s) 908 .delta. 2.28(3H, s), 4.84(2H, s), 7.11(1H, br-s),
7.48(1H, t, J=7.8Hz), 7.55(1H, s), 7.59(1H, s), 7.64-7.68(3H, m),
8.01(1H, br-s) 909 .delta.1.24(6H, d, J=6.8Hz), 2.33(3H, s),
2.86(1H, septet, J=6.8Hz), 4.85(2H, s), 7.09(1H, s), 7.16(1H, br),
7.33(1H, d, J=2.0Hz), 7.48(1H, t, J=7.8Hz), 7.60(1H, s),
7.67-7.69(2H, m), 8.00(1H, s) 910 .delta. 2.23(3H, s), 4.86(2H, s),
6.51(1H, s), 6.78(1H, d, J=2.4Hz), 7.15(1H, br.), 7.49(1H, br.),
7.51(1H, t, J=7.8), 7.56(1H, s), 7.71(1H, d, J=6.8Hz), 8.05(1H, s)
911 .delta. 1.29(6H, d, J=7.3Hz), 2.98(1H, septet, J=7.3Hz),
4.85(2H, s), 7.10(1H, br), 7.47-7.52(2H, m), 7.56-7.58(2H, m),
7.65(1H, d, J=7.3Hz), 7.72(1H, br), 7.96(1H, s) 912 .delta.
2.37(3H, s), 4.85(2H, s), 4.88(2H, s), 7.06(1H, br), 7.16(1H, d,
J=2.4Hz), 7.43(1H, d, J=2.4Hz), 7.50(1H, t, =7.8Hz), 7.56(1H, s),
7.68(1H, s), 7.70(1H, s), 8.03(1H, s) 913 (DMSO-d.sub.6).delta.
4.96(2H, s), 7.49(1H, t, J=7.8Hz), 7.64(1H, d, J=7.8Hz), 7.71(1H,
d, J=7.8Hz), 8.02(1H, d, J=2.0Hz), 8.10(1H, s), 8.30(1H, d,
J=2.0Hz), 10.34(1H, s), 10.38(1H, s) 914 (DMSO-d.sub.6).delta.
1.29(6H, d, J=6.8Hz), 2.99(1H, septet, J=6.8Hz), 4.86(2H, s),
7.42(1H, t, J=7.8Hz), 7.52(1H, d, J=1.5Hz), 7.68(1H, d, J=7.8Hz),
7.74(1H, d, J=1.5Hz), 7.85(1H, d, J=7.8Hz), 8.09(1H, s), 9.27(1H,
s), 9.66(1H, s) 915 .delta. 4.85(2H, s), 7.04(1H, br),
7.47-7.55(2H, m), 7.63-7.70(3H, m), 7.90(1H, d, J=1.5Hz), 7.99(1H,
s) 916 (DMSO-d6).delta. 4.86(2H, s), 7.43(1H, t, J=7.8Hz), 7.70(1H,
d, J=7.8Hz), 7.84(1H, d, J=7.8Hz), 8.10(1H, s), 9.46(1H, br-s),
9.73(1H, br-s) 917 .delta. 2.22(6H, s), 3.79(2H, t, J=5.4Hz),
4.42(2H, t, J=5.4Hz), 7.37(1H, t, J=7.8Hz), 7.44(2H, s), 7.63(1H,
d, J=7.8Hz), 7.71(1H, d, J=7.8Hz), 8.12(1H, br-s), 9.37(1H, s),
9.60(1H, br-s) 918 .delta. 2.34(6H, s), 2.53-2.56(2H, m), 4.43(2H,
t, J=6.3Hz), 6.80(1H, br-s), 7.41(1H, s), 7.47(2H, s), 7.50(1H, s),
7.62-7.64(2H, m), 7.9(1H, s) 919 (DMSO-d.sub.6).delta.
2.66-2.78(2H, m), 4.34(2H, t, J=5.9Hz), 7.49(1H, t, J=7.8Hz),
7.66-7.72(2H, m), 8.12(1H, s), 8.30(2H, s), 10.00(1H, s), 10.60(1H,
s) 920 .delta. 1.32(6H, d, J=6.1Hz), 2.51(3H, s), 5.01-5.07(1H, m),
6.72(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.54-7.57(2H, m), 7.64(1H, d,
J=8.1Hz), 7.71(2H, d, J=7.3Hz), 7.85(1H, s), 8.01-8.03(1H, m),
8.13(1H, s), 8.45-8.48(1H, m) 921 .delta.1.32(6H, d, J=6.1Hz),
1.74-1.77(2H, m), 1.84-1.87(2H, m), 2.74(2H, t, J=6.4Hz), 3.02(2H,
q, J=6.4Hz), 5.04(1H, septet, J=6.1Hz), 6.73(1H, br s),
7.42-7.46(2H, m), 7.52-7.55(1H, m), 7.62(1H, br s, J=8Hz), 7.76(1H,
br s), 7.96(1H, br s), 8.03-8.06(1H, m) 922 .delta.1.31(6H, d,
J=6.4Hz), 1.68-1.76(4H, m), 2.81(2H, t, J=5.7Hz), 2.99(2H, q,
J=6.1Hz), 5.03(1H, septet, J=6.4Hz), 6.73(1H, br-s), 7.43-7.47(2H,
m), 7.59-7.64(3H, m), 8.03(1H, s) 923 .delta.1.31(6H, d, J=6.4Hz),
3.83(3H, s), 5.02(1H, septet, J=6.4Hz), 6.55(1H, s), 6.78(1H,
br-s), 7.41-7.50(2H, m), 7.57(1H, d, J=7.8Hz), 8.03(1H, br-s),
8.08(1H, br- s) 924 .delta.1.32(6H, d, J=6.3Hz), 3.86(3H, s),
5.04(1H, septet, J=6.3Hz), 6.72(1H, br-s), 7.45-7.53(2H, m),
7.63(1H, d, J=7.3Hz), 7.80(1H, br-s), 8.14(1H, br-s) 925
.delta.1.32(6H, d, J=5.9Hz), 3.89(3H, s), 5.04(1H, septet,
J=5.9Hz), 6.72(1H, s), 7.47-7.50(2H, m), 7.70(1H, d, J=8.3Hz),
7.90(1H, br-s), 8.14(1H, br-s) 926 .delta.1.32(6H, d, J=6.1Hz),
3.88(3H, s), 3.93(3H, s), 5.04(1H, septet), 6.78(1H, br- s),
7.47(1H, br-s), 7.64-7.68(2H, m), 8.05(1H, br-s), 9.40(1H, br-s)
927 .delta.1.33(6H, d, J=5.9Hz), 2.34(3H, s), 5.02(1H, septet,
J=5.9Hz), 6.74(1H, br-s), 7.24(1H, s), 7.44(1H, t, J=7.8Hz),
7.49-7.52(1H, m), 7.58-7.60(1H, m), 7.82(1H, br-s), 8.07(1H, br-s),
8.71(1H, s) 928 .delta.1.31(6H, d, J=6.4Hz), 2.35(3H, s),
5.01-5.07(1H, m), 6.74(1H, br-s), 7.25(1H, s), 7.46(1H, t,
J=7.8Hz), 7.58-7.63(2H, m), 7.68(1H, br-s), 8.07(1H, br-s) 929
.delta.1.32(6H, d, J=5.9Hz), 5.03(1H, septet, J=5.9Hz), 6.52(1H,
septet, J=6.3Hz), 6.71(1H, br-s), 6.99(1H, d, J=8.8Hz), 7.43(1H, t,
J=7.8Hz), 7.51-7.58(2H, m), 7.92(1H, br-s), 8.01(1H, br-s),
8.14(1H, dd, J=8.8Hz, 2.4Hz), 8.34(1H, d, J=2.4Hz) 930
.delta.1.32(6H, d, J=5.9Hz), 2.33(3H, s), 5.50(1H, septet,
J=5.9Hz), 6.53(1H, septet, J=6.4Hz), 6.74(1H, br-s), 6.87(1H, s),
7.43(1H, t, J=7.8Hz), 7.54-7.58(2H, m), 7.64(1H, br-s), 8.04(1H,
br-s), 8.37(1H, s) 931 .delta.1.32(6H, d, J=6.3Hz), 5.05(1H,
septet, J=6.3Hz), 6.30(1H, septet, J=6.3Hz), 6.69(1H, br-s),
7.01(1H, d, J=8.8Hz), 7.47(1H, t, J=7.8Hz), 7.56(1H, dd, J=7.8Hz,
1.5Hz), 7.68(1H, d, J=7.8Hz), 7.98(1H, br-s), 8.27(1H, br-s),
8.82(1H, d, J=8.8Hz) 932 .delta.1.32(6H, d, J=6.4Hz), 2.29(3H, s),
2.41(3H, s), 5.04(1H, septet, J=6.4Hz), 6.58(1H, septet, J=6.4Hz),
6.72(2H, s), 7.37-7.46(2H, m), 7.53-7.57(1H, m), 7.60(1H, d,
J=7.8Hz), 8.05(1H, br-s) 933 .delta. 2.49(3H, s), 4.85(2H, s),
7.16(1H, br-s), 7.48-7.57(3H, s), 7.70(2H, s), 7.76(1H, d,
J=7.6Hz), 7.92(1H, s), 8.00(1H, dd, J=3.4Hz, 6.8Hz), 8.13(1H, s),
8.47(1H, dd, J=3.4Hz, 6.8Hz) 934 .delta.1.75-1.79(2H, m),
1.84-1.87(2H, m), 2.74(2H, t, J=6.4Hz), 3.02(2H, q, J=6.4Hz),
4.85(2H, s), 7.13(1H, br s), 7.41-7.51(2H, m), 7.59-7.69(2H, m),
7.76(1H, br s), 8.00(1H, br s), 8.06(1H, br d, J=8.5Hz) 935
.delta.1.65-1.76(4H, m), 2.81(2H, t, J=6.1Hz), 2.99(2H, q,
J=6.4Hz), 4.85(2H, s), 7.10(1H, br-s), 7.48-7.52(2H, m), 7.59(1H,
s), 7.67-7.69(2H, m), 8.04(1H, s) 936 .delta.3.86(3H, s), 4.85(2H,
s), 6.58(1H, s), 7.10(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.60(1H, d,
J=7.8Hz), 7.65(1H, d, J=7.8Hz), 7.84(1H, br-s), 8.10(1H, br-s) 937
.delta.3.85(3H, s), 4.85(2H, s), 7.16(1H, br-s), 7.51(1H, t,
J=7.9Hz), 7.62(1H, d, J=7.9Hz), 7.68(1H, d, J=7.9Hz), 7.85(1H,
br-s), 8.12(1H, br-s) 938 .delta.3.87(3H, s), 4.85(2H, s), 7.21(1H,
br-s), 7.51(1H, t, J=8.3Hz), 7.61(1H, d, J=8.3Hz), 7.68(1H, d,
J=8.3Hz), 7.92(1H, br-s), 8.13(1H, br-s) 939 .delta.3.89(3H, s),
3.94(3H, s), 4.86(2H, s), 7.20(1H, br-s), 7.52(1H, t, J=7.8Hz),
7.70-7.73(2H, m), 8.09(1H, br-s), 9.44(1H, s) 940 .delta.4.87(2H,
s), 7.07-7.11(2H, m), 7.31-7.34(1H, m), 7.47-7.52(2H, m),
7.67-7.69(1H, m), 8.01(1H, dd, J=8.0Hz, 1.4Hz), 8.19(1H, br-s),
8.58-8.60(1H, m), 11.3(1H, br-s) 941 .delta.4.84(2H, s), 7.19(1H,
br-s), 7.33(1H, dd, J=8.3Hz, 4.8Hz), 7.44(1H, t, J=8.3Hz),
7.58-7.59(2H, m), 7.94-7.97(2H, m), 8.44(1H, dd, J=4.8Hz, 1.4Hz),
9.14(1H, br-s) 942 .delta. 2.44(3H, s), 4.86(2H, s), 7.11(1H,
br-s), 7.52(1H, t, J=7.8Hz), 7.59(1H, d, J=2.9Hz), 7.63-7.65(2H,
m), 7.76(1H, s), 8.09(1H, s), 9.23(1H, s) 943 .delta.4.85(2H, s),
6.52(1H, septet, J=6.3Hz), 6.99(1H, d, J=8.8Hz), 7.07(1H, br-s),
7.48(1H, t, J=8.3Hz), 7.61-7.62(2H, m), 7.86(1H, s), 8.02(1H, s),
8.15(1H, dd, J=8.8Hz, 2.5Hz), 8.33(1H, d, J=2.5Hz) 944 .delta.
2.35(3H, s), 4.85(2H, s), 6.55(1H, septet, J=6.4Hz), 6.89(1H, s),
7.08(1H, br-s), 7.49(1H, t, J=7.8Hz), 7.59(1H, s), 7.63(2H, d,
J=8.3Hz), 8.05(1H, s), 8.40(1H, s) 945 .delta. 2.34(3H, s),
4.85(2H, s), 7.17(1H, br-s), 7.22-7.26(1H, m), 7.49(1H, t,
J=7.8Hz), 7.60-7.66(2H, m), 7.75(1H, br-s), 8.07(1H, br-s),
8.73(1H, br-s) 946 .delta.4.86(2H, s), 7.13(1H, br-s), 7.52(1H, t,
J=8.3Hz), 7.67(1H, d, J=8.3Hz), 7.74(1H, d, J=8.3Hz), 8.02(1H, s),
8.05(1H, s), 8.66(1H, s), 8.70(1H, br-s) 947 .delta. 2.36(3H, s),
5.05(2H, s), 7.16(1H, br-s), 7.25(1H, s), 7.51(1H, t, J=7.8Hz),
7.68-7.70(3H, m), 8.08(1H, br-s) 948 .delta.4.86(2H, s), 6.30(1H,
septet, J=6.4Hz), 7.00(1H, d, J=8.8Hz), 7.04(1H, br-s), 7.52(1H, t,
J=7.8Hz), 7.63(1H, dd, J=7.8Hz, 1.5Hz), 7.70(1H, d, J=7.8Hz),
8.04(1H, br-s), 8.27(1H, br-s), 8.83(1H, d, J=8.8Hz) 992 .delta.
2.37(3H, s), 4.85(2H, s), 6.33(1H, septet, J=5.8Hz), 6.87(1H, s),
7.05(1H, br-s), 7.49-7.53(2H, m), 7.66-7.68(2H, m), 8.05(1H, s)
1010 .delta.1.33(6H, d, J=6.4Hz), 2.37(3H, s), 5.04(1H, septet,
J=6.4Hz), 6.34(1H, septet, J=6.4Hz), 6.72(1H, br-s), 6.88(1H, s),
7.45(1H, t, J=7.8Hz), 7.58-7.64(3H, m), 8.05(1H, s) 1039 .delta.
2.38(3H, s), 4.86(2H, s), 6.34(1H, septet), 6.89(1H, s), 7.09(1H,
br-s), 7.51(1H, t, J=7.8Hz), 7.57(1H, br-s), 7.66(1H, br-s),
7.68(1H, d, J=7.8Hz), 8.07(1H, s) 1086 .delta. 2.37(3H, s),
4.85(2H, s), 6.33(1H, septet, J=5.8Hz), 6.87(1H, s), 7.05(1H,
br-s), 7.49-7.53(2H, m), 7.66-7.68(2H, m), 8.05(1H, s) 1104
.delta.1.32(6H, d, J=6.4Hz), 2.29(3H, s), 2.41(3H, s), 5.04(1H,
septet, J=6.4Hz), 6.58(1H, septet, J=6.4Hz), 6.72(2H, s),
7.37-7.46(2H, m), 7.53-7.57(1H, m), 7.60(1H, d, J=7.8Hz), 8.05(1H,
br-s) 1180 .delta. 2.46(3H, s), 4.86(2H, s), 7.11(1H, s),
7.51-7.86(5H, m), 8.10(1H, br-s) 1198 .delta. 1.31(6H, d, J=6.3Hz),
2.40(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.42-7.47(2H,
m), 7.56(1H, s), 7.60-7.63(2H, m), 7.74(1H, s), 8.03(1H, s) 1227
.delta. 2.41(3H, s), 4.85(2H, s), 7.05(1H, br), 7.44(1H, s),
7.51(1H, t, J=8.1Hz), 7.57(1H, s), 7.67-7.70(3H, m), 8.05(1H, s)
1245 .delta. 1.31(6H, d, J=6.1Hz), 2.42(3H, s), 5.04(1H, septet,
J=6.1Hz), 6.71(1H, s), 7.45(1H, d, J=8.1Hz), 7.48(1H, s),
7.61-7.64(2H, m), 7.72-7.74(2H, m), 8.04(1H, s)
1274 .delta. 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.48-7.53(2H,
m), 7.68-7.73(4H, m), 8.06(1H, s) 1292 .delta. 1.32(6H, d,
J=6.3Hz), 2.42(3H, s), 5.04(1H, septet, J=6.3Hz), 6.72(1H, s),
7.44-7.52(2H, m), 7.62-7.66(3H, m), 7.93(1H, s), 8.04(1H, s) 1321
.delta. 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.50-7.54(2H, m),
7.63(1H, s), 7.70-7.72(2H, m), 7.94(1H, s), 8.08(1H, s) 1361
.delta. 0.87(3H, t, J=7.3Hz), 1.53-1.63(2H, m), 2.44-2.56(2H, m),
2.64(2H, t, J=7.8Hz), 4.38(2H, t, J=6.3Hz), 7.16(1H, s), 7.38(1H,
t, J=7.8Hz), 7.48(1H, s), 7.61-7.64(2H, m), 7.91-7.94(2H, m),
8.00(1H, s) 1368 .delta. 0.93(3H, t, J=7.3Hz), 1.59-1.69(2H, m),
2.71(2H, t, J=7.8Hz), 4.86(2H, s), 7.11(1H, br), 7.49-7.54(2H, m),
7.62(1H, s), 7.69-7.72(2H, m), 7.96(1H, d, J=1.5Hz), 8.07(1H, s)
1385 .delta. 2.35(3H, s), 2.44(3H, s), 4.86(2H, s), 6.74(1H, s),
7.34-7.38(3H, m), 7.46(1H, s), 7.52(1H, d, J=8.8Hz), 7.89(1H, s),
8.35(1H, d, J=8.8Hz) 1386 .delta. 1.32(6H, d, J=6.3Hz), 2.40(6H,
s), 2.41(3H, s), 5.03(1H, septet, J=6.3Hz), 6.46(1H, br-s),
7.15(1H, s), 7.28-7.37(4H, m), 7.95(1H, d, J=8.3Hz) 1387 .delta.
2.40(6H, s), 2.45(3H, s), 4.86(2H, s), 6.80(1H, br), 7.16(1H, s),
7.32-7.42(4H, m), 7.85(1H, br) 1388 .delta.1.35(3H, t, J=7.3Hz),
2.36(6H, s), 4.28(2H, q, J=7.3Hz), 6.91(1H, s), 7.29(1H, t,
J=8.3Hz), 7.37(2H, s), 7.74-7.79(2H, m), 8.32(1H, br-d, J=5.9Hz)
1389 .delta.1.34(6H, d, J=6.3Hz), 2.36(6H, s), 5.07(1H, septet,
J=6.3Hz), 6.86(1H, br-s), 7.30(1H, t, J=8.1Hz), 7.37(2H, s),
7.72-7.79(2H, m), 8.32(1H, br) 1408 .delta. 2.37(6H, s), 4.70(4H,
dt, J=2.0Hz, 46.8Hz), 5.28(1H, tt, J=4.4Hz, 24.9Hz), 7.08(1H,
br-s), 7.33(1H, t, J=8.3Hz), 7.37(2H, s), 7.76(1H, d, J=12.2Hz),
7.81(1H, dt, J=1.4Hz, 7.8Hz), 8.29(1H, br-s) 1411 .delta. 2.37(6H,
s), 2.51-2.62(2H, m), 4.46(2H, t, J=6.4Hz), 6.97(1H, br- s),
7.32(1H, t, J=8.3Hz), 7.37(2H, s), 7.74-7.82(2H, m), 8.28(1H, br-s)
1416 .delta. 2.37(6H, s), 3.76-3.79(2H, m), 4.49(2H, t, J=5.4Hz),
7.02(1H, br), 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.74-7.81(2H, m),
8.30(1H, br) 1418 .delta. 2.37(6H, s), 4.88(2H, s), 7.21(1H, br),
7.32-7.37(3H, m), 7.76-7.85(2H, m), 8.31(1H, br) 1421 .delta.
2.36(6H, s), 3.60(2H, t, J=5.9Hz), 4.54(2H, t, J=5.9Hz), 7.03(1H,
br), 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.76-7.81(2H, m), 8.29(1H,
br) 1435 .delta.1.35(3H, t, J=7.3Hz), 2.36(6H, s), 4.29(2H, q,
J=7.3Hz), 6.89(1H, br-s), 7.30(1H, t, J=7.8Hz), 7.35(2H, s),
7.74-7.78(2H, m), 8.32(1H, br-s) 1455 .delta. 2.33(6H, s), 4.70(4H,
ddd, J=48.8Hz, 2.4Hz, 4.3Hz), 5.28(1H, tt, J=20.0, 4.3Hz), 7.08(1H,
br-s), 7.32(1H, d, J=8.3Hz), 7.35(2H, s), 7.75-7.83(2H, m),
8.29(1H, br-s) 1458 .delta. 2.36(6H, s), 2.51-2.62(2H, m), 4.47(2H,
t, J=6.3Hz), 6.95(1H, br- s), 7.32(1H, t, J=7.3Hz), 7.35(2H, s),
7.74-7.82(2H, m), 8.29(1H, br-s) 1463 .delta. 2.36(6H, s), 3.77(2H,
t, J=5.4Hz), 4.49(2H, t, J=5.4Hz), 7.03(1H, br), 7.31(1H, t,
J=8.3Hz), 7.35(2H, s), 7.76-7.80(2H, m), 8.29(1H, br) 1465 .delta.
2.36(6H, s), 4.88(2H, s), 7.18(1H, br), 7.35(1H, t, J=8.3Hz),
7.36(2H, s), 7.75-7.85(2H, m), 8.31(1H, br) 1898 .delta. 1.33(6H,
d, J=6.3Hz), 2.37(3H, s), 5.05(1H, septet, J=6.3Hz), 7.21(1H,
br-s), 7.32(1H, d, J=6.6Hz), 7.39(1H, t, J=8.1Hz), 7.46(1H, s),
7.50-7.53(2H, m), 8.30-8.36(2H, m) 1899 .delta. 2.38(3H, s),
4.87(2H, s), 7.40-7.51(5H, m), 7.62(1H, s), 8.27-8.30(2H, m) 1900
.delta. 1.34(6H, d, J=6.1Hz), 2.41(6H, s), 5.05(1H, septet,
J=6.1Hz), 7.22-7.26(2H, m), 7.31-7.40(4H, m), 8.33(1H, dd, J=1.5Hz,
8.1Hz) 1901 .delta. 2.40(6H, s), 4.88(2H, s), 7.29(1H, s), 7.37(2H,
s), 7.38-7.43(2H, m), 7.50(1H, s), 8.28(1H, d, J=6.8Hz) 1902
.delta. 4.88(2H, s), 7.39(1H, dd, J=1.5Hz, 7.3Hz), 7.44-7.51(2H,
m), 7.88-7.92(2H, m), 8.03(1H, s), 8.36(1H, d, J=8.3Hz), 8.70(1H,
d, J=8.3Hz) 1903 .delta. 2.37(3H, s), 4.88(2H, s), 6.55(1H, septet,
J=6.3Hz), 6.90(1H, s), 7.32(1H, s), 7.41-7.48(3H, m), 8.31(1H,
br-s), 8.49(1H, s) 1904 .delta. 1.34(6H, d, J=6.3Hz), 2.44(6H, s),
5.05(1H, septet, J=6.3Hz), 7.13(1H, s), 7.25-7.28(2H, m), 7.37(2H,
s), 7.41(1H, t, J=8.3Hz), 8.31(1H, dd, J=1.5Hz, 8.3Hz) 1905 .delta.
2.44(6H, s), 4.88(2H, s), 7.15(1H, br), 7.33-7.37(3H, m),
7.43-7.53(2H, m), 8.25(1H, d, J=8.3Hz) 1906 .delta. 2.40(3H, s),
4.86(2H, s), 7.05-7.10(2H, m), 7.47(1H, s), 7.53(1H, d, J=8.8Hz),
7.58(1H, br), 8.22(1H, br), 8.28(1H, d, J=8.8Hz). 1907 .delta.
2.40(6H, s), 4.86(2H, s), 7.00-7.11(3H, m), 7.37(2H, s), 8.18(1H,
br) 1908 .delta. 1.33(6H, d, J=6.3Hz), 2.39(6H, s), 5.04(1H,
septet, J=6.3Hz), 6.81(1H, br), 7.30(1H, br), 7.37(2H, s), 8.23(1H,
br) 1909 .delta. 1.33(6H, d, J=6.1Hz), 2.34(3H, s), 2.42(3H, s),
5.05(1H, septet, J=6.1Hz), 6.46(1H, br), 7.30(1H, d, J=8.1Hz),
7.45(1H, s), 7.49(1H, d, J=8.5Hz), 7.60(1H, dd, J=1.7Hz, 8.1Hz),
7.83(1H, s), 8.27(1H, d, J=8.5Hz), 8.46(1H, br) 1910 .delta.
2.39(3H, s), 2.42(3H, s), 4.86(2H, s), 6.77(1H, br), 7.35(1H, d,
J=8.1Hz), 7.46(1H, s), 7.50(1H, d, J=8.8Hz), 7.65(1H, dd, J=2.0Hz,
8.1Hz), 7.80(1H, s), 8.27(1H, d, J=8.8Hz), 8.36(1H, br) 1911
.delta. 1.33(6H, d, J=6.3Hz), 2.34(9H, s), 5.04(1H, septet,
J=6.3Hz), 6.48(1H, br-s), 7.31(1H, d, J=7.8Hz), 7.34(2H, s),
7.55(1H, s), 7.64(1H, dd, J=1.5Hz, 7.8Hz), 8.46(1H, s) 1912 .delta.
2.34(6H, s), 2.40(3H, s), 4.86(2H, s), 6.78(1H, br), 7.34-7.36(3H,
m), 7.50(1H, s), 7.69(1H, dd, J=1.5Hz, 7.8Hz), 8.36(1H, s) 1913
.delta.1.32(6H, d, J=6.3Hz), 2.43(3H, s), 3.96(3H, s), 5.05(1H,
sept., J=6.3Hz), 6.98(1H, d, J=8.5Hz), 7.24(1H, s), 7.44(1H, s),
7.49(1H, d, J=8.5Hz), 7.71(1H, dd, J=2.2Hz, 8.5Hz), 7.82(1H, s),
8.25(1H, d, J=8.5Hz), 8.68(1H, s) 1914 .delta. 2.43(3H, s),
4.00(3H, s), 4.87(2H, s), 7.02(1H, d, J=8.5Hz), 7.45(1H, s),
7.50(1H, d, J=8.5Hz), 7.54(1H, s), 7.74-7.79(2H, m), 8.28(1H, d,
J=8.5Hz), 8.66(1H, s) 1915 .delta. 1.33(6H, d, J=6.3Hz), 2.42(3H,
s), 5.00-5.10(1H, m), 6.91(1H, br), 7.20(1H, dd, J=8.5Hz, 10.5Hz),
7.46(1H, s), 7.49(1H, d, J=8.8Hz), 7.62-7.66(1H, m), 7.82(1H, s),
8.20(1H, d, J=8.8Hz), 8.71(1H, d, J=6.1Hz) 1916 .delta. 2.46(3H,
s), 4.87(2H, s), 7.23-7.29(2H, m), 7.47(1H, s), 7.51(1H, d,
J=8.8Hz), 7.68-7.73(1H, m), 7.78(1H, s), 8.23(1H, d, J=8.5Hz),
8.68(1H, d, J=6.1Hz) 1917 .delta. 1.33(6H, d, J=6.3Hz), 2.34(6H,
s), 5.04(1H, septet, J=6.3Hz), 6.91(1H, s), 7.20(1H, dd, J=8.5Hz,
10.5Hz), 7.35(2H, s), 7.56(1H, s), 7.66-7.70(1H, m), 8.71(1H, br-d,
J=6.6Hz) 1918 .delta. 2.34(6H, s), 4.87(2H, s), 7.22(1H, dd,
J=8.8Hz, 10.5Hz), 7.32(2H, s), 7.75-7.79(1H, m), 7.87(1H, s),
8.56(1H, s), 8.63(1H, br) 1919 .delta.1.34(6H, d, J=6.3Hz),
2.43(3H, s), 5.06(1H, septet, J=6.3Hz), 7.21(1H, s), 7.46(1H, s),
7.49-7.52(2H, m), 7.61(1H, dd, J=2.2Hz, 8.5Hz), 7.82(1H, s),
8.24(1H, d, J=8.5Hz), 8.78(1H, d, J=2.2Hz) 1920 .delta. 2.43(3H,
s), 4.88(2H, s), 7.47(1H, s), 7.50-7.57(3H, m), 7.66(1H, dd,
J=2.0Hz, 8.3Hz), 7.78(1H, s), 8.26(1H, d, J=8.3Hz), 8.72(1H, s)
1921 .delta. 1.34(6H, d, J=6.1Hz), 2.34(6H, s), 5.05(1H, septet,
J=6.1Hz), 7.23(1H, s), 7.35(2H, s), 7.51(1H, d, J=8.3Hz),
7.63-7.69(2H, m), 8.76(1H, s) 1922 .delta. 2.35(6H, s), 4.88(2H,
s), 7.36(2H, s), 7.50(1H, br), 7.53-7.59(2H, m), 7.70(1H, dd,
J=2.0Hz, 8.3Hz), 8.72(1H, s) 1923 .delta. 2.35(6H, s), 2.45(3H, s),
4.84(2H, s), 7.00(1H, br), 7.36(2H, s), 7.41(1H, s), 7.48(2H, s),
7.83(1H, s) 1924 .delta. 1.33(6H, d, J=6.1Hz), 2.46(3H, s),
5.05(1H, septet, J=6.1Hz), 6.89(1H, br-s), 7.48(1H, s), 7.51(1H, d,
J=9.1Hz), 7.79(2H, s), 7.89(1H, s), 8.18(1H, d, J=9.1Hz), 8.19(1H,
s) 1925 .delta. 2.43(3H, s), 4.86(2H, s), 7.31(1H, br-s), 7.49(1H,
s), 7.52(1H, d, J=8.8Hz), 7.78(1H, s), 7.85(1H, s), 7.94(1H, s),
8.18(1H, d, J=8.8Hz), 8.24(1H, s) 1926 .delta. 1.32(6H, d,
J=6.1Hz), 2.34(6H, s), 5.04(1H, septet, J=6.1Hz), 6.87(1H, s),
7.36(2H, s), 7.50(1H, s), 7.83(1H, s), 7.90(1H, s), 8.20(1H, s)
1927 .delta. 2.35(6H, s), 4.86(2H, s), 7.26(1H, s), 7.37(2H, s),
7.48(1H, s), 7.89(1H, s), 7.97(1H, s), 8.24(1H, s) 1928
.delta.1.31(6H, d, J=6.3Hz), 2.33(6H, s), 3.89(2H, br.),
4.97-5.04(1H, m), 6.59(1H, s), 6.92(1H, s), 7.02(1H, s),
7.23-7.26(1H, m), 7.34(2H, s), 7.39(1H, br) 1929 .delta. 2.35(6H,
s), 3.04(6H, s), 4.84(2H, s), 6.94(2H, br), 7.04(1H, s), 7.30(1H,
s), 7.349(2H, s), 7.404(1H, s) 1930 .delta. 1.30(6H, d, J=6.3Hz),
2.37(3H, s), 2.48(3H, s), 5.02(1H, septet, J=6.3Hz), 6.57(1H, s),
7.20-7.28(2H, m), 7.44(2H, s), 7.50(1H, d, J=8.3Hz), 7.76(1H, s),
8.28(1H, d, J=9.1Hz) 1931 .delta. 2.39(3H, s), 2.48(3H, s),
4.84(2H, s), 7.22(1H, d, J=8.3Hz), 7.44-7.54(3H, m), 7.80(1H, s),
8.13(1H, d, J=8.1Hz), 8.20(1H, s), 9.04(1H, s) 1932 .delta.
1.30(6H, d, J=6.1Hz), 2.39(6H, s), 2.48(3H, s), 5.02(1H, septet,
J=6.1Hz), 6.63(1H, s), 7.19-7.25(3H, m), 7.36(2H, s), 7.81(1H, s)
1933 .delta. 2.40(6H, s), 2.50(3H, s), 4.84(2H, s), 7.01(1H, br-s),
7.18(1H, s), 7.24-7.27(1H, m), 7.31-7.34(1H, m), 7.37(2H, s),
7.82(1H, s) 1934 .delta. 1.31(6H, d, J=6.1Hz), 2.41(3H, s),
5.04(1H, septet, J=6.1Hz), 6.69(1H, s), 7.16-7.21(1H, m), 7.46(1H,
s), 7.5(1H, d, J=8.8Hz), 7.88(1H, dd, J=2.9Hz, 6.6Hz), 7.96(1H,
br), 8.40(1H, d, J=8.8Hz), 8.57(1H, d, J=17.6Hz) 1935 .delta.
2.42(3H, s), 4.84(2H, s), 7.04(1H, br), 7.20-7.27(1H, m), 7.46(1H,
s), 7.51(1H, d, J=8.5Hz), 7.94(1H, br), 8.01(1H, dd, J=2.9Hz,
6.6Hz), 8.40(1H, d, J=8.5Hz), 8.57(1H, br-d, J=17.6Hz) 1936 .delta.
1.31(6H, d, J=6.3Hz), 2.35(6H, s), 5.02(1H, septet, J=6.3Hz),
6.70(1H, s), 7.19(1H, dd, J=9.0Hz, 11.2Hz), 7.36(2H, s), 7.83(1H,
dd, J=2.9Hz, 6.6Hz), 7.99(1H, br), 8.01(1H, d, J=5.1Hz) 1937
.delta. 2.36(6H, s), 4.84(2H, s), 7.10(1H, br-s), 7.21-7.26(1H, m),
7.36(2H, s), 7.94-8.03(3H, m) 1938 .delta. 1.31(6H, d, J=6.3Hz),
2.41(3H, s), 5.03(1H, septet, J=6.3Hz), 6.68(1H, s), 7.40(1H, d,
J=8.8Hz), 7.46(1H, s), 7.51(1H, d, J=8.5Hz), 7.67(1H, d, J=8.5Hz),
7.78(1H, d, J=2.7Hz), 8.06(1H, s), 8.32(1H, d, J=8.8Hz) 1939
.delta. 2.42(3H, s), 4.84(2H, s), 7.38(1H, d, J=8.8Hz),
7.45-7.49(2H, m), 7.72(1H, d, J=7.3Hz), 7.93(1H, s), 8.17(1H, d,
J=8.5Hz), 8.52(1H, s), 9.43(1H, s) 1940 .delta. 1.31(6H, d,
J=6.1Hz), 2.40(6H, s), 5.03(1H, septet, J=6.1Hz), 6.70(1H, s),
7.36(2H, s), 7.41(1H, d, J=8.8Hz), 7.63-7.66(2H, m), 7.75(1H, d,
J=2.7Hz) 1941 .delta. 2.40(6H, s), 4.84(2H, s), 7.08(1H, br),
7.37(2H, s), 7.46(1H, d, J=8.8Hz), 7.64-7.70(2H, m), 7.82(1H, d,
J=2.7Hz) 1942 .delta.1.31(6H, d, J=6.3Hz), 2.41(3H, s),
4.97-5.07(1H, m), 6.70(1H, s), 7.45-7.58(4H, m), 7.72-7.75(2H, m),
8.30(1H, d, J=8.8Hz) 1943 .delta. 2.44(3H, s), 4.85(2H, s),
7.43-7.47(2H, m), 7.54(1H, d, J=8.5Hz), 7.61(1H, d, J=8.5Hz),
7.86(1H, s), 7.99(1H, d, J=8.1Hz), 9.09(1H, s), 9.89(1H, s) 1944
.delta. 2.43(3H, s), 4.84(2H, s), 7.36(1H, s), 7.44(1H, s),
7.47(1H, d, J=8.5Hz), 7.79(2H, d, J=8.5Hz), 8.08(1H, d, J=8.5Hz),
8.62(1H, s), 9.65(1H, s) 1945 .delta. 1.31(6H, d, J=6.3Hz),
2.45(6H, s), 5.03(1H, septet, J=6.3Hz), 6.66(1H, s), 7.16-7.21(2H,
m), 7.36(2H, s), 7.76(1H, s), 7.82(1H, dd, J=2.7Hz, 8.8Hz) 1946
.delta.1.52(9H, s), 2.41(3H, s), 6.58(1H, s), 7.19(1H, dd, J=2.7Hz,
8.5Hz), 7.41(1H, s), 7.45(1H, s), 7.51(1H, d, J=7.1Hz), 7.69(1H,
s), 7.79(1H, d, J=8.5Hz), 8.30(1H, d, J=8.5Hz) 1947 .delta.
2.44(3H, s), 2.45(3H, s), 4.83(2H, d, J=1.7Hz), 7.00(1H, br),
7.07-7.27(2H, m), 7.36(2H, s), 7.74-7.77(1H, d, J=10.3Hz), 7.86(1H,
dd, J=8.5Hz, 10.3Hz) 1948 .delta.3.45(3H, s), 4.80(2H, s),
7.53-7.57(2H, m), 7.68(1H, s), 7.82(1H, d, J=7.8Hz), 7.93-7.95(3H,
m) 1949 .delta. 2.30(3H, s), 3.41(3H, s), 4.77(2H, s), 6.77(1H,
s),
6.95-7.00(1H, m), 7.07-7.16(2H, m), 7.29-7.41(4H, m) 1950 .delta.
1.26(6H, d, J=5.9Hz), 2.28(6H, s), 3.33(3H, s), 4.96(1H, septet,
J=5.9Hz), 6.47(1H, s), 6.88(1H, d, J=7.8Hz), 7.04(1H, t, J=7.8Hz),
7.21(2H, s), 7.23-7.47(2H, m) 1951 .delta. 2.29(6H, s), 3.34(3H,
s), 4.77(2H, s), 6.81(1H, br), 6.99(1H, d, J=7.8Hz), 7.10(1H, t,
J=7.8Hz), 7.22(2H, s), 7.24-7.26(1H, m), 7.42(1H, s) 1954 .delta.
1.26(6H, d, J=6.3Hz), 2.34(3H, s), 3.34(3H, s), 4.97(1H, septet,
J=6.3Hz), 6.46(1H, s), 6.99(1H, d, J=7.8Hz), 7.07(1H, t, J=7.8Hz),
7.28-7.31(2H, m), 7.40-7.44(1H, m), 7.62(1H, s) 1955 .delta.
2.35(3H, s), 3.36(3H, s), 4.77(2H, s), 7.02-7.13(3H, m),
7.29-7.37(2H, m), 7.44-7.52(1H, m), 7.62(1H, s) 1956 .delta.
1.26(3H, t, J=7.3Hz), 2.29(6H, s), 3.86(2H, q, J=7.3Hz), 4.76(2H,
s), 6.86(1H, br), 6.92-6.95(1H, m), 7.08(1H, t, J=8.1Hz), 7.22(2H,
s), 7.23-7.30(1H, m), 7.38(1H, t, J=2.0Hz) 1957 .delta. 1.46(6H, d,
J=6.3Hz), 2.07(6H, s), 4.77(2H, s), 5.40(1H, septet, J=6.3Hz),
6.78(1H, br), 6.98(1H, d, J=7.8Hz), 7.14-7.19(1H, m), 7.17(2H, s),
7.29(1H, s), 7.46(1H, d, J=7.8Hz) 1958 .delta. 2.34(6H, s),
3.45(3H, s), 4.80(2H, s), 7.36(2H, s), 7.50-7.56(3H, m), 7.78(1H,
d, J=6.1Hz), 7.90(1H, s) 1959 (DMSO-d.sub.6) .delta. 2.32(6H, s),
3.30(3H, s), 4.86(2H, s), 6.83(1H, t, J=7.4Hz), 7.40(1H, t,
J=7.4Hz), 7.44(2H, s), 7.67(1H, t, J=7.4Hz), 10.05(1H, s) 1960
.delta.1.29(6H, d, J=6.3Hz), 2.35(6H, s), 3.35(3H, s), 3.38(3H, s),
4.97-5.03(1H, m), 7.36(2H, s), 7.58(1H, s), 7.76(1H, s), 7.84(1H,
s), 8.56(1H, s) 1961 (DMSO-d.sub.6) .delta. 2.28(6H, s), 2.33(3H,
s), 7.44(2H, s), 7.48(1H, t, J=7.8Hz), 7.66-7.75(2H, m), 8.11(1H,
t, J=2.0Hz), 9.96(1H, s), 10.56(1H, s) 1962 (DMSO-d.sub.6)
.delta.1.34(3H, t, J=7.3Hz), 2.34(6H, s), 2.96(2H, q, J=7.3Hz),
7.33(2H, s), 7.41(1H, t, J=7.8Hz), 7.67(1H, d, J=7.8Hz),
7.83-7.85(1H, m), 8.11(1H, d, J=2.0Hz), 8.79(1H, s), 9.58(1H, s)
1963 .delta. 1.32(6H, d, J=6.6Hz), 2.37(6H, s), 5.00-5.06(1H, m),
6.69(1H, s), 7.35-7.65(5H, m), 8.09(1H, s), 8.72(1H, s) 1964
.delta. 2.37(6H, s), 4.85(2H, s), 7.07(1H, br.), 7.39(2H, s),
7.45(1H, t, J=8.1Hz), 7.61-7.68(2H, m), 8.11(1H, s), 8.69(1H, s)
1967 .delta.1.34(6H, d, J=6.3Hz), 2.34(6H, s), 5.09(1H, septet,
J=6.3Hz), 7.29(1H, br-s), 7.35(2H, s), 7.91(1H, t, J=7.8Hz),
7.97(1H, d, J=7.8Hz), 8.21(1H, d, J=7.8Hz), 9.19(1H, br-s) 1968
.delta. 2.35(6H, s), 4.89(2H, s), 7.36(2H, s), 7.63(1H, br-s),
7.97(1H, dd, J=8.3Hz, 7.6Hz), 8.05(1H, d, J=7.6Hz), 8.21(1H, d,
J=8.3Hz), 9.17(1H, br-s) 1969 .delta. 2.35(6H, s), 3.77-3.80(2H,
m), 4.48-4.52(2H, m), 7.36(2H, s), 7.46(1H, br-s), 7.94(1H, t,
J=7.8Hz), 8.02(1H, dd, J=7.8Hz, 1.0Hz), 8.19(1H, dd, J=7.8Hz,
1.0Hz), 9.17(1H, br-s) 2061 .delta.1.36(6H, d, J=6.4Hz), 2.52(6H,
s), 5.07-5.14(1H, m), 7.36(2H, s), 7.56(1H, t, J=8.2Hz), 8.15(1H,
dd, J=8.2Hz, 1.9Hz), 8.44(1H, dd, J=8.2Hz, 1.9Hz), 9.45(1H, br-s),
12.9(1H, br-s) 2062 .delta. 2.37(6H, s), 4.91(2H, s), 7.36(2H, s),
7.61(1H, t, J=8.3Hz), 8.23(1H, dd, J=8.3Hz, 1.9Hz), 8.45(1H, dd,
J=8.3Hz, 1.9Hz), 9.81(1H, br-s), 12.7(1H, br-s) 2157 .delta.
2.36(6H, s), 4.90(2H, s), 7.38(2H, s), 7.52-7.60(2H, m), 8.44(1H,
s), 8.56(1H, d, J=5.4Hz), 8.58(1H, br-s) 2164 .delta.1.33(6H, d,
J=5.8Hz), 2.35(6H, s), 5.03-5.07(1H, m), 7.06(1H, s), 7.35(2H, s),
7.93(1H, d, J=2.4Hz), 7.95(1H, d, J=5.9Hz, 2.4Hz), 8.49(1H, d,
J=5.9Hz), 9.58(1H, br-s) 2165 (DMSO-d.sub.6).delta. 2.26(6H, s),
5.02(2H, s), 7.43(2H, s), 7.75(1H, dd, J=5.4Hz, 2.0Hz), 8.31(1H, d,
J=2.0Hz), 8.60(1H, d, J=5.4Hz), 10.41(1H, br-s), 10.92(1H, br-s)
2167 (DMSO-d.sub.6).delta. 2.36(6H, s), 4.90(2H, s), 7.34(2H, s),
7.94(1H, dd, J=7.3Hz, 3.4Hz), 8.31(1H, d, J=7.3Hz), 8.60(1H, d,
J=3.4Hz), 10.90(1H, br-s), 13.65(1H, br-s) 2168
(DMSO-d.sub.6).delta. 2.30(6H, s), 3.61(3H, s), 5.03(2H, s),
7.47(2H, s), 7.92(1H, d, J=7.6Hz), 7.98(1H, d, J=7.6Hz), 8.08(1H,
t, J=7.6Hz), 10.18(1H, s) I-1 .delta. 2.34(6H, s), 3.87(2H, br-s),
6.86-6.89(1H, m), 7.21-7.30(3H, m), 7.33(2H, s), 7.39(1H, s) I-2
.delta. 3.87(2H, br), 6.84-7.00(1H, m), 7.14-7.17(1H, m), 7.20(1H,
t, J=2.0Hz), 7.24-7.28(1H, m), 7.60(2H, d, J=8.8Hz), 7.78(2H, d,
J=8.8Hz), 7.90(1H, br-s) I-3 .delta. 2.51(3H, d, J=8.8Hz), 3.86(2H,
br-s), 6.83-8.68(1H, m), 7.13-7.25(3H, m), 7.26-7.63(3H, m),
7.90(1H, br-s) I-4 .delta.3.87(2H, br-s), 3.89(3H, s),
6.86-6.88(1H, m), 6.99(1H, dd, J=8.6Hz, 2.0Hz), 7.15-7.20(2H, m),
7.27(1H, t, J=7.8Hz), 7.51(1H, d, J=8.6Hz), 7.83(1H, s), 7.93(1H,
s) I-5 .delta.3.89(2H, br-s), 6.86-6.89(1H, m), 7.12-7.30(3H, m),
7.52-7.59(2H, m), 7.76-7.93(2H, m) I-6 .delta. 2.43(3H, s),
3.83(2H, br), 6.85-6.88(1H, m), 7.14-7.17(1H, m), 7.21-7.29(2H, m),
7.45(1H, s), 7.49(1H, d, J=8.8Hz), 7.76(1H, br), 8.27(1H, d,
J=8.8Hz) I-7 .delta. 2.34(6H, s), 3.87(2H, br), 6.86-6.89(1H, m),
7.20-7.35(6H, m) I-8 .delta. 2.42(3H, s), 3.79(2H, br-s), 6.80(1H,
dd, J=2.2Hz, 7.8Hz), 6.90(1H, d, J=7.8Hz), 7.05(1H, s), 7.15(1H, t,
J=7.8Hz), 7.26-7.44(7H, m), 7.53(1H, s) I-9 .delta. 2.33(3H, s),
2.52(3H, d, J=8.8Hz), 3.89(2H, br-s), 6.86-6.89(1H, m),
7.14-7.16(1H, m), 7.22(1H, s), 7.28-7.30(2H, m), 7.65(1H, br-s),
8.11(1H, s) I-10 .delta. 2.28(3H, s), 2.46(3H, d, J=6.1Hz),
3.88(2H, br-s), 6.84-6.89(1H, m), 7.15-7.19(1H, m), 7.23-7.29(2H,
m), 7.41(1H, d, J=9.1Hz), 7.73(1H, br-s), 7.81(1H, d, J=9.1Hz) I-12
.delta. 2.60(3H, s), 3.92(2H, br-s), 6.89-6.92(1H, m),
7.24-7.32(3H, m), 7.46(1H, s), 7.76(1H, br-s) I-13 .delta. 2.27(6H,
s), 3.31(3H, s), 6.40-6.43(1H, m), 6.54-6.58(1H, m), 6.71(1H, t,
J=2.0Hz), 6.76-6.86(1H, m), 7.22(2H, s) I-14 .delta. 1.45(6H, d,
J=6.3Hz), 2.07(6H, s), 3.53(2H, br), 5.37(1H, septet, J=6.3Hz),
6.56-6.63(3H, m), 6.96(1H, t, J=7.8Hz), 7.16(2H, s) I-15 .delta.
1.32(3H, t, J=7.6Hz), 2.72(2H, q, J=7.6Hz), 3.88(2H, br),
6.85-6.89(1H, m), 7.13-7.14(1H, m), 7.22-7.30(2H, m), 7.46(1H, s),
7.50(1H, d, J=8.8Hz), 7.80(1H, br-s), 8.29(1H, d, J=8.8Hz) I-16
.delta. 1.17(3H, t, J=7.6Hz), 2.28(3H, s), 2.65(2H, q, J=7.6Hz),
3.85(2H, br-s), 6.82-6.85(1H, m), 7.21-7.23(3H, m), 7.34(2H, s),
7.64(1H, s) I-17 .delta. 1.22(6H, t, J=7.6Hz), 2.69(4H, q,
J=7.6Hz), 3.86(2H, br-s), 6.86-6.89(1H, m), 7.15-7.36(4H, m),
7.38(2H, s) I-18 .delta. 1.23(3H, t, J=7.3Hz), 2.76(2H, q,
J=7.3Hz), 3.88(2H, br-s), 6.88-6.91(1H, m), 7.26-7.32(3H, m),
7.50(1H, s), 7.53(1H, s), 7.95(1H, d, J=1.5Hz) I-19 .delta.
1.00(3H, t, J=7.3Hz), 1.65-1.75(2H, m), 2.67(2H, t, J=7.3Hz),
3.89(2H, br), 6.84-6.88(1H, m), 7.11-7.29(3H, m), 7.43(1H, s),
7.49(1H, d, J=8.5Hz), 7.85(1H, br-s), 8.27(1H, d, J=7.8Hz) I-20
.delta.1.22(6H, d, J=6.8Hz), 2.32(3H, s), 3.17(1H, septet,
J=6.8Hz), 3.87(2H, br-s), 6.85-6.93(1H, m), 7.20-7.29(3H, m),
7.35(1H, s), 7.40-7.45(2H, m). I-21 .delta. 2.35(3H, s), 3.85(5H,
s), 6.85-6.89(1H, m), 6.95(1H, s), 7.13(1H, s), 7.23-7.30(3H, m),
7.62(1H, s) I-22 .delta. 1.25(3H, t, J=7.6Hz), 2.76(2H, q,
J=7.6Hz), 3.88(2H, br-s), 6.87-6.91(1H, m), 7.24-7.31(3H, m),
7.47(1H, s), 7.55(1H, s), 7.57(1H, s) I-23 .delta. 2.62(3H, d,
J=6.4Hz), 3.91(2H, br-s), 6.89(1H, d, J=8.0Hz), 7.20-7.32(4H, m),
7.49(1H, d, J=9.0Hz), 8.58-8.60(1H, m) I-24 .delta.3.91(2H, br-s),
3.92(3H, s), 6.89-6.92(1H, m), 7.21-7.33(3H, m), 7.59(1H, d,
J=1.2Hz), 8.50(1H, s), 8.54(1H, s) I-25 .delta. 2.35(3H, s),
2.57(3H, d, J=6.8Hz), 3.88(2H, br-s), 6.88-6.91(1H, m),
7.25-7.34(4H, m), 7.67(1H, s) I-26 .delta. 2.41(3H, s), 3.88(2H,
br-s), 6.87-6.91(1H, m), 7.25-7.31(3H, m), 7.47(1H, s), 7.65(1H,
s), 7.72(1H, s) I-27 .delta. 1.23(3H, t, J=7.3Hz), 2.74(2H, q,
J=7.3Hz), 3.87(2H, br-s), 6.86-6.91(1H, m), 7.25-7.31(3H, m),
7.50(1H, s), 7.59(1H, s), 7.73(1H, d, J=1.5Hz) I-28
(DMSO-d.sub.6).delta. 0.84(3H, t, J=7.3Hz), 1.48-1.58(2H, m),
2.66(2H, t, J=7.3Hz), 5.36(2H, br-s), 6.77(1H, dd, J=1.0Hz, 7.8Hz),
7.10-7.19(3H, m), 7.59(1H, s), 7.80(1H, s), 10.03(1H, s) I-29
.delta. 0.90(3H, t, J=7.3Hz), 1.25-1.37(2H, m), 1.55-1.63(2H, m),
2.72(2H, t, J=7.8Hz), 3.89(2H, br), 6.87-6.91(1H, m), 7.24-7.31(3H,
m), 7.48(1H, s), 7.55(1H, s), 7.73(1H, d, J=1.5Hz) I-30 .delta.
2.39(3H, s), 2.66(3H, d, J=6.9Hz), 7.43(1H, s), 7.75-7.79(2H, m),
8.33(1H, d, J=8.3Hz), 8.48(1H, d, J=8.3Hz), 8.80(1H, s) I-31
.delta. 2.41(3H, s), 3.88(2H, s), 6.86-6.91(1H, m), 7.28-7.32(3H,
m), 7.49(1H, s), 7.58(1H, s), 7.93(1H, d, J=1.2Hz) I-32 .delta.
0.91(3H, t, J=7.3Hz), 1.58-1.67(2H, m), 2.69(2H, t, J=7.8Hz),
3.88(2H, br-s), 6.87-6.90(1H, m), 7.26-7.31(3H, m), 7.50(1H, s),
7.54(1H, s), 7.95(1H, d, J=2.0Hz) I-33 .delta. 2.33(6H, s),
3.87(2H, br-s), 6.86-6.89(1H, m), 7.21-7.29(3H, m), 7.34(2H, s),
7.52(1H, s) I-34 .delta. 2.32(6H, s), 3.86(2H, br-s), 6.85-6.88(1H,
m), 7.20-7.28(3H, m), 7.33(2H, s), 7.60(1H, s) I-35 .delta.
3.86(2H, br), 6.84-6.87(1H, m), 7.13-7.28(3H, m), 7.63-7.64(2H, m),
7.70-7.74(2H, m), 7.91(1H, br-s) I-36 .delta. 3.99(2H, br-s),
6.85-6.88(1H, m), 7.23-7.34(3H, m), 7.91(2H, s), 8.69(1H, s) I-37
.delta. 3.91(2H, br), 6.88-6.91(1H, m), 7.15-7.21(2H, m), 7.29(1H,
t, J=7.8Hz), 7.94-7.98(2H, m), 8.03(2H, d, J=8.8Hz), 8.11(1H, s)
I-38 (DMSO-d.sub.6).delta. 5.39(2H, br-s), 6.77-6.80(1H, m),
7.12-7.19(3H, m), 8.49(2H, s), 10.53(1H, s) I-39
(DMSO-d.sub.6).delta. 2.30(3H, s), 4.32(2H, br-s), 4.39(2H, q,
J=8.3Hz), 6.79-6.86(3H, m), 7.18-7.27(2H, m), 7.45(1H, d, J=8.8Hz),
7.56(1H, s), 8.91(1H, br-s) I-40 .delta.3.87(2H, br-s),
6.85-6.88(1H, m), 7.14(1H, dd, J=9.3Hz, 1.0Hz), 7.19(1H, t,
J=2.0Hz), 7.27(1H, t, J=7.9Hz), 7.64(2H, d, J=8.7Hz), 7.71(2H, d,
J=8.7Hz), 7.86(1H, s) I-42 .delta.3.88(2H, s), 6.90(1H, d,
J=6.8Hz), 7.23-7.32(3H, m), 7.60(1H, s), 7.92(2H, s) I-43
.delta.3.89(2H, br-s), 6.90(1H, dt, J=2.5Hz, 6.3Hz), 7.25-7.32(3H,
m), 7.59(1H, s), 7.72(2H, s) I-44 .delta.3.89(2H, br-s), 6.90(1H,
dt, J=2.5Hz, 6.4Hz), 7.28-7.30(3H, m), 7.60(1H, s), 7.93(2H, s)
I-45 .delta.3.92(2H, s), 6.92(1H, dt, J=1.5Hz, 7.3Hz),
7.23-7.30(3H, m), 7.79(1H, s), 8.04(2H, s) I-46 .delta.3.89(2H,
br-s), 6.90(1H, dd, J=2.4Hz, 4.9Hz), 7.23-7.32(3H, m), 7.61(1H, s),
7.93(2H, s) I-47 .delta.3.88(2H, br-s), 6.90(1H, d, J=6.3Hz),
7.23-7.32(3H, m), 7.62(1H, s), 7.92(2H, s) I-48
.delta.6.90-6.94(1H, m), 7.28-7.33(3H, m), 7.73(1H, s), 8.02(1H,
s), 8.25(1H, s) I-49 .delta. 2.31(6H, s), 2.90(3H, s), 6.81(1H, dd,
J=1.9Hz, 7.8Hz), 7.15-7.18(2H, m), 7.30(1H, t, J=7.8Hz), 7.42(1H,
s), 7.52(2H, s) I-50 .delta. 2.91(3H, s), 6.82-6.85(1H, m),
7.21-7.23(2H, m), 7.32(1H, t, J=7.8Hz), 7.64(1H, s), 7.93(2H, s)
I-51 .delta. 2.29(3H, s), 2.34(3H, s), 3.82(2H, br), 6.81(1H, d,
J=8.1Hz), 6.92(1H, d, J=8.1Hz), 7.11(1H, t, J=7.8Hz), 7.41-7.44(2H,
m), 7.50(1H, d, J=8.3Hz), 8.36(1H, d, J=8.3Hz) I-53 .delta.
2.23(3H, s), 2.39(3H, s), 3.82(2H, br), 7.10-7.16(2H, m), 7.24(1H,
d, J=1.7Hz), 7.44(1H, s), 7.49(1H, d, J=8.1Hz), 7.73(1H, s),
8.30(1H, d, J=8.8Hz) I-55 .delta. 2.34(3H, s), 2.40(3H, s),
3.70(2H, br), 6.72(1H, dd, J=2.4Hz, 8.1Hz), 6.83(1H, d, J=2.4Hz),
7.07(1H, d, J=8.1Hz), 7.36(1H, s), 7.44(1H, s), 7.50(1H, d,
J=8.5Hz), 8.30(1H, d, J=8.5Hz) I-56 .delta. 2.38(6H, s), 2.42(3H,
s), 3.70(2H, br), 6.72(1H, dd, J=2.4Hz, 8.1Hz), 6.89(1H, d,
J=2.4Hz), 7.05(1H, s), 7.07(1H, d, J=8.1Hz), 7.36(2H, s) I-59
.delta. 2.37(6H, s), 3.90(2H, br-s), 6.96-7.01(1H, m), 7.10(1H, t,
J=7.8Hz), 7.36(2H, s), 7.43-7.47(1H, m), 7.86(1H, d, J=13.2Hz) I-60
.delta. 2.33(6H, s), 6.99(1H, dt, J=1.5Hz, 7.8Hz), 7.10(1H, t,
J=7.8Hz), 7.43(2H, s), 7.46(1H, d, J=7.8Hz), 7.84(1H, d, J=13.2Hz)
I-61 .delta. 2.33(6H, s), 3.93(2H, s), 7.05-7.14(1H, m),
7.17-7.21(1H, m), 7.31(1H, s), 7.35(2H, s), 7.37-7.40(1H, m) I-62
.delta. 2.40(3H, s), 3.77(2H, br), 6.79-6.83(1H, m), 6.97-7.03(1H,
m), 7.44-7.51(3H, m), 8.42(1H, d, J=8.8Hz), 8.60(1H, br-d,
J=18.8Hz) I-63 .delta. 2.35(6H, s), 3.74(2H, br-s), 6.77-6.83(1H,
m), 7.01(1H, dd,
J=8.8Hz, 11.7Hz), 7.35(2H, s), 7.42(1H, dd, J=2.9Hz, 6.6Hz),
8.01(1H, d, J=15.6Hz) I-64 .delta. 2.38(3H, s), 4.27(2H, br),
6.89(1H, dd, J=1.5Hz, 8.1Hz), 7.05(1H, d, J=8.8Hz), 7.18(1H, t,
J=8.1Hz), 7.45(1H, s), 7.51(1H, d, J=8.1Hz), 7.60(1H, s), 8.34(1H,
d, J=8.8Hz) I-65 .delta. 2.40(6H, s), 4.27(2H, br-s), 6.88(1H, dd,
J=1.5Hz, 7.8Hz), 7.03(1H, dd, J=1.5Hz, 7.8Hz), 7.16(1H, t,
J=7.8Hz), 7.29(1H, s), 7.36(2H, s) I-66 .delta. 2.39(3H, s),
4.27(2H, br), 7.08(1H, dd, J=2.2Hz, 8.3Hz), 7.32-7.36(2H, m),
7.45(1H, s), 7.50(1H, d, J=8.5Hz), 7.68(1H, s), 8.24(1H, d,
J=8.5Hz) I-67 .delta. 2.33(6H, s), 4.27(2H, br-s), 7.15(1H, d,
J=8.1Hz), 7.35-7.38(5H, m) I-68 .delta. 2.41(3H, s), 3.87(2H, br),
6.73(1H, dd, J=2.9Hz, 8.5Hz), 7.18(1H, d, J=2.9Hz), 7.21(1H, d,
J=8.8Hz), 7.45(1H, s), 7.50(1H, d, J=8.8Hz), 8.12(1H, s), 8.34(1H,
d, J=8.5Hz) I-69 .delta. 2.39(6H, s), 3.85(2H, br-s), 6.72(1H, dd,
J=2.7Hz, 8.5Hz), 7.15(1H, d, J=2.7Hz), 7.22(1H, d, J=8.5Hz),
7.36(2H, s), 7.66(1H, s) I-70 .delta. 2.43(6H, s), 4.34(2H, br),
6.86(1H, dd, J=1.5Hz, 8.3Hz), 6.96(1H, dd, J=1.5Hz, 8.3Hz),
7.13(1H, s), 7.19(1H, t, J=8.3Hz), 7.36(2H, s) I-71 .delta.
2.41(3H, s), 3.87(2H, br), 6.66(1H, dd, J=2.9Hz, 8.5Hz), 7.03(1H,
d, J=2.9Hz), 7.38(1H, d, J=8.5Hz), 7.45(1H, s), 7.50(1H, d,
J=8.5Hz), 7.75(1H, br-s), 8.33(1H, d, J=8.5Hz) I-72 .delta.
2.40(3H, s), 3.94(2H, br), 7.05-7.16(2H, m), 7.36(1H, dd, J=2.2Hz,
8.5Hz), 7.45(1H, s), 7.50(1H, d, J=9.0Hz), 7.66(1H, s), 8.24(1H, d,
J=9.0Hz) I-73 .delta. 2.41(3H, s), 3.88(2H, br-s), 6.54(1H, dd,
J=2.9Hz, 8.5Hz), 6.88(1H, d, J=2.9Hz), 7.37(1H, s), 7.45(1H, s),
7.52(1H, d, J=8.3Hz), 7.61(1H, d, J=8.3Hz), 8.32(1H, d, J=8.5Hz)
I-74 .delta. 2.44(6H, s), 3.86(2H, br-s), 6.52(1H, dd, J=2.9Hz,
8.5Hz), 6.91(1H, d, J=2.9Hz), 7.12(1H, s), 7.35(2H, s), 7.62(1H, d,
J=8.5Hz) I-75 .delta. 2.38(3H, s), 4.39(2H, s), 7.06(1H, s),
7.40(1H, d, J=1.7Hz), 7.43-7.50(3H, m), 7.90(1H, d, J=9.1Hz),
8.73(1H, s) I-76 .delta. 2.27(6H, s), 4.09(2H, br-s), 7.08(1H, s),
7.33(2H, s), 7.37(1H, s), 7.43(1H, s), 7.83(1H, s) I-77 .delta.
2.39(3H, s), 2.93(3H, s), 3.95(2H, br), 6.84(1H, d, J=8.3Hz),
7.21-7.27(2H, m), 7.44(1H, s), 7.48(1H, d, J=8.5Hz), 7.69(1H, s),
8.28(1H, d, J=8.5Hz) I-79 .delta. 2.33(6H, s), 3.76(4H, br),
6.19(1H, d, J=2.0Hz), 6.60(2H, d, J=2.0Hz), 7.34(1H, br), 7.52(2H,
s) I-80 .delta. 2.38(3H, s), 4.65(2H, s), 7.26(1H, s), 7.34(1H, s),
7.47(1H, s), 7.52(1H, d, J=8.5Hz), 8.20(1H, d, J=8.5Hz) I-81
.delta. 2.50(3H, s), 3.90(2H, s), 6.91-6.94(1H, m), 7.27-7.35(3H,
m), 7.48-7.57(2H, m), 7.70(1H, s), 7.75(1H, s), 8.01-8.04(1H, m),
8.45-8.48(1H, m) I-82 .delta.1.74-1.78(2H, m), 1.82-1.88(2H, m),
2.72(2H, t, J=6.0Hz), 3.01(2H, q, J=6.0Hz), 3.88(2H, br-s),
6.85-6.88(1H, m), 7.14-7.16(1H, m), 7.22-7.29(2H, m), 7.42(1H, d,
J=8.6Hz), 7.70(1H, br-s), 8.10(1H, d, J=9.0Hz) I-83
.delta.1.71-1.79(4H, m), 2.81(2H, t, J=6.1Hz), 2.99(2H, q,
J=6.3Hz), 3.87(2H, br-s), 6.87-6.90(1H, m), 7.24-7.29(3H, m),
7.47-7.52(2H, m) I-84 .delta.3.87(2H, br-s), 6.51(1H, septet,
J=6.3Hz), 6.85-6.88(1H, m), 6.99(1H, d, J=8.7Hz), 7.15(1H, d,
J=7.3Hz), 7.20(1H, t, J=2.0Hz), 7.25-7.29(1H, m), 7.75(1H, br-s),
8.15(1H, dd, J=8.7Hz, 2.4Hz), 8.30(1H, d, J=2.4Hz) I-85 .delta.
2.37(3H, s), 4.27(2H, br-s), 6.55(1H, septet, J=6.3Hz),
6.88-6.91(2H, m), 7.06(1H, dd, J=7.3Hz, 1.5Hz), 7.18(1H, t,
J=7.3Hz), 7.37(1H, br-s), 8.50(1H, br-s) I-86 .delta. 2.37(3H, s),
3.88(2H, br-s), 6.34(1H, septet, J=6.3Hz), 6.88(1H, s),
6.89-6.91(1H, m), 7.23-7.31(3H, m), 7.47(1H, br-s)
[0144] The insecticides containing the compounds represented by
formula (1) of the present invention as active ingredients are
suitable for preventing insect pests such agricultural,
horticultural and stored grain insect pests which are noxious to
paddy rice, fruit trees, vegetables, other crops and flowing
plants, sanitary pests, or nematodes. For example, the insecticides
have strong insecticidal activity on the following insect pests:
Lepidoptera such as cotton caterpillar (Diaphania indica), oriental
tea tortrix (Homona magnanima), cabbage webworm (Hellulla undalis),
summer fruit tortrix(Adoxophyes orana fasciata), smaller tea
tortrix (Adoxophyes sp.), apple tortrix (Archips fuscocupreanus),
peach fruit moth (Carposina niponensis), Manchurian fruit moth
(Grapholita inopinata), oriental fruit moth (Grapholita molesta),
soybean pod borer (Leguminivora glycinivorella), mulberry
leafroller (Olethreutes mori), citrus leafminer (Phyllocnistis
citrella), persimmon fruit moth (Stathmopoda masinissa), tea
leafroller (Caloptilia theivora), Caloptilia sp. (Caloptilia
zachrysa), apple leafminer (Phyllonorycter ringoniella), pear
barkminer (Spulerrina astaurota), small citrus dog (Papilio
xuthus), common cabbage worm (Pieris rapae crucivora), tabacco
budworm (Heliothis armigera), codling moth (Lapsey resia
pomonella), diamondback moth (Plutella xylostella), apple fruit
moth (Argyresthia conjugella), peach fruit moth (Carposina
niponensis), rice stem borer (Chilo suppressalis), rice leafroller
(Cnaphalocrocis medinalis), tabacco moth (Ephestia elutella),
mulberry pyralid (Glyphodes pyloalis), paddy borer (Scirpophaga
incertulas), rice skipper (Parnara guttata), rice armyworm
(Pseudaletia separata), pink borer (Sesamia inferens), cabbage
armyworm (Mamestra brassicae), common cutworm (Spodoptera litura),
beet armyworm (Spodoptera exigua), black cutworm (Agrotis ipsilon),
turnip moth (Agrotis segetum), beet semi-looper (Autographa
nigrisigna), and cabbage looper (Trichoplusia ni); hemiptera such
as aster leafHopper (Macrosteles fascifrons), green rice leafHopper
(Nephotettix cincticeps), brown rice planthopper (Nilaparvata
lugens), small brown planthopper (Laodelphax striatellus),
whitebacked rice planthopper (Sogatella furcifera), citrus psylla
(Diaphorina citri), grape whitefly (Aleurolobus taonabae),
silverleaf whitefly (Bermisia argentifolii), sweetpotato whitefly
(Bemisia tabaci), greenHouse whitefly (Trialeurodes vaporariorum),
turnip aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii),
apple aphid (Aphis Citricola), green peach aphid (Myzus persicae),
Indian wax scale (Ceroplastes ceriferus), Comstock mealybug
(Pseudococcus Comstocki), Japanese mealybug (Planococcus
kraunhiae), cottony citrus scale (Pulvinaria aurantii), camphor
scale (Pseudaonidia duplex), San Jose scale (Comstockaspis
perniciosa), arrowHead scale (Unaspis yanonensis), brownwinged
green bug (Plautia Stali), and brown marmorated stink bug
(Halyomorpha mista); Coleoptera such as soybean beetle (Anomala
rufocuprea), Japanese beetle (Popillia japonica), cigarette beetle
(Lasioderma serricorne), powderpost beetle (Lyctusbrunneus),
twenty-eight-spotted ladybird (Epilachna vigintioctopunctata),
adzuki been weevil (Callosobruchus chinensis), vegetable weevil
(Listroderes costirostris), maize weevil (Sitophilus zeamais), boll
weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus
oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice
leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta
striolata), pine shoot beetle (Tomicus piniperda), Colorado potato
beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna
varivestis), corn rootworm (Diabrotica sp.), yellowspotted
longicorn beetle (Psacothea hilaris), and whitespotted longicorn
beetle (Anoplophora malasiaca); Diptera such as melon fly
(Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae),
onion maggot (Delia antiqua), seedcorn maggot (Delia platura),
soybean pod gall midge (Asphondylia sp.), house fly (Musca
domestica), garden pea leafminer (Chromatomyia horticola), legume
leafminer (Liriomyza trifolii), bryony leafminer (Liriomyza
bryoniae), and common house mosquito (Culex pipiens pipiens);
Nematoda such as coffee root-lesion nematode (Pratylenchus
coffeae), root-lesion nematode (Pratylenchus sp.), potato cyst
nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne
sp.), citrus nematode (Tylemchulus semipenetrans), nematode
(Aphelenchus avenae), and chrysanthemum foliar nematode
(Aphelenchoides ritzemabosi); Thysanoptera such as melon thrips
(Thrips palmi), western flower thrips (Frankliniella occidentalis),
yellow tea thrips (Scirtothrips dorsalis), honeysuckle thrips
(Thrips flavus), and onion thrips (Thrips tabaci); Orthoptera such
as German cockroach (Blattella germanica), American cockroach
(Periplaneta americana), and rice grasshopper (Oxya yezoensis).
[0145] The insecticides containing the compounds represented by
formula (1) of the present invention as active ingredients have a
significant preventive effect on the above-described insect pests
noxious to lowland crops, dry field crops, fruit trees, vegetables,
other crops, and flowering plants. The effect as the insecticides
of the present invention can be achieved by treating paddy water,
foliages or soil of paddy fields, dry fields, fruit trees,
vegetables, other crops, or flowering plants before the breeding of
noxious insects or at the time of observation of the breeding of
noxious insects at the predicted breeding season of noxious
insects.
[0146] The insecticides of the present invention are generally
formed into formulations suitable for use according to a normal
method for formulating agricultural/Horticultural pesticides.
Namely, a compound represented by formula (1) may be mixed with an
appropriate inert carrier, and if required, an auxiliary at a
proper proportion, and the resultant mixture is subjected to
dissolution, separation, suspension, mixing, impregnation,
adsorption or adhesion to form a suitable formulation such as a
suspension, an emulsion, a liquid drug, a wettable powder, a
granule, a dusting powder, or a tablet. As the inert carrier used
in the present invention, either a solid or a liquid may be used.
Examples of a material usable as the solid carrier include soybean
flour, grain flour, wood flour, bark flour, sawing flour, tobacco
stalk flour, walnut sHell flour, bran, cellulose powder, a residue
after plant extraction, a synthetic polymer such as a synthetic
resin powder, clay (for example, kaoline, bentonite, or acid white
clay), talc (for example, talc or pyrophyllite), silica (for
example, diatomite, silica powder, mica, white carbon (synthetic
high-dispersion silicate referred to as "hydrous silicate fine
powder" or "hydrous silicate", some products containing calcium
silicate as main components)), activated carbon, sulfur powder,
pumice, calcined diatomite, brick powder, fly ash, sand, inorganic
mineral powders such as calcium carbonate and calcium phosphate,
chemical fertilizers such as ammonium sulfate, ammonium phosphate,
ammonoium nitrate, urea, and ammonium chloride, and compost. These
carriers are used alone or in a mixture of at least two kinds.
[0147] As a material usable as the liquid carrier, a material
having a solvent ability or a material having no solvent ability
but having an ability to disperse an active ingredient compound
with the aid of an auxiliary is selected. Typical examples of the
liquid carrier are given below, and these examples can be used
alone or in a mixture of two more kinds. Examples of the liquid
carrier include water, alcohols (for example, methanol, ethanol,
isopropanol, butanol, and ethylene glycol); ketones (for example,
acetone, methylethyl ketone, methyl isobutyl ketone, diisobutyl
ketone, and cyclohexanone); ethers (for example, diethyl ether,
dioxane, cellosolve, diisopropyl ether, and tetrahydrofuran);
aliphatic hydrocarbons (for example, kerosine and mineral oil);
aromatic hydrocarbons (for example, benzene, toluene, xylene,
solvent naphtha, and alkylnaphthalene); halogenated hydrocarbons
(for example, dichloromethane, chloroform, carbon tetrachloride,
and chlorobenzene); esters (for example, ethyl acetate, butyl
acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate,
and dioctyl phthalate); amides (for example, dimethylformamide,
diethylformamide, and dimethylacetamide); and nitriles (for
example, acetonitrile).
[0148] Typical examples of other auxiliaries are given below, and
these examples are used alone or in combination according to
purposes. The auxiliary is not necessarily used. For example, a
surfactant is used for emulsifying, dispersing, solubilizing and/or
wetting the active ingredient compound. Examples of the surfactant
include
[0149] polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl
ether, polyoxyethylene higher fatty acid esters, polyoxyethylene
resin acid esters, polyoxyethylene sorbitan monolaurate,
polyoxyethylene sorbitan monooleate, alkylaryl sulfonate,
naphthalenesulfonate, lignin-sulfonate, higher alcohol sulfates.
Examples of other auxiliaries used for stabilizing dispersion of
the active ingredient compound, and tackifying and/or bonding the
active ingredient compound are given below. Examples of such
auxiliaries include casein, gelatin, starch, methyl cellulose,
carboxymethyl cellulose, gum arabic, polyvinyl alcohol, wood
turpentine, bran oil, bentonite, xanthan gum, and
lignin-sulfonate.
[0150] Another auxiliary for improving fluidity of a solid product
can also be used. Examples of such an auxiliary include wax,
stearates, and alkyl phosphates. Also, an auxiliary such as a
naphthalenesulfonic acid condensate or condensed phosphate, can be
used as a deflocculant for a suspending product. Furthermore, an
auxiliary such as silicone oil can be used as a defoaming
agent.
[0151] The compounds represented by formula (1) of the present
invention are stable to light, heat and oxidation. However, an
appropriate amount of an antioxidant or an ultraviolet absorber,
for example, a phenol derivative such as BHT
(2,6-di-t-butyl-4-methyl phenol) or BHA (butylated hydroxyanisole),
a bisphenol derivative, an arylamine such as
phenyl-.alpha.-naphthylamine, phenyl-.beta.-naphthylamine, or a
condensate of phenetidine and acetone, or a benzophenone compound,
may be added as a stabilizer to produce compositions having a
stable effect.
[0152] When a compound represented by formula (1) of the present
invention is used as an active ingredient, generally, the amount
thereof used in a dust is 0.5% by weight to 20% by weight, the
amount in an emulsion is 5% by weight to 50% by weight, the amount
in a wettable powder is 10% by weight to 90% by weight, the amount
in a granule is 0.1% by weight to 20% by weight, and the amount in
a flowable formulation is 10% by weight to 90% by weight. With
respect to the amount of the carrier in a formulation, the amount
in a dust is 60% by weight to 99% by weight, the amount in an
emulsion is 40% by weight to 95% by weight, the amount in a
wettable powder is 10% by weight to 90% by weight, the amount in a
granule is 80% by weight to 99% by weight, and the amount in a
flowable formulation is 10% by weight to 90% by weight. With
respect to the amount of the auxiliary in a formulation, the amount
in a dust is 0.1% by weight to 20% by weight, the amount in an
emulsion is 1% by weight to 20% by weight, the amount in a wettable
powder is 0.1% by weight to 20% by weight, the amount in a granule
is 0.1% by weight to 20% by weight, and the amount in a flowable
formulation is 0.1% by weight to 20% by weight.
[0153] In order to prevent various noxious insects, the compound of
the present invention is directly used or properly diluted with
water or suspended in water, and an effective amount thereof for
preventing pests is applied to crops in which the breeding of the
noxious insects is predicted, or a place where the breeding of the
noxious insects is undesirable. The amount of the compound used
depends upon the various factors, for example, the purpose, the
object insects, the growth conditions of crops, the breeding
tendency of insects, weather, environmental conditions,
formulations, application methods, application places, and
application times. However, the content of the active ingredient
used is generally 0.0001 ppm to 5000 ppm, and preferably 0.01 ppm
to 1000 ppm. The amount of the active ingredient per 10a is
generally 1 g to 300 g.
[0154] An insecticide containing as an active ingredient the
compounds represented by formula (1) of the present invention may
be singly used for preventing insect pests such agricultural,
horticultural or stored grain insect pests which are noxious to
paddy rice, fruit trees, vegetables, other crops and flowering
plants, sanitary pests, or nematodes. In order to further obtain an
excellent preventive effect on various noxious insects which
simultaneously occur, at least one of other insecticides and/or
fungicides may be combined with the compounds represented by
formula (1) of the present invention.
[0155] Examples of such insecticides which can be combined with the
compounds represented by formula (1) of the present invention
include synthetic pyrethroid insecticides such as allethrin,
tetramethrin, resmethrin, phenothrin, furamethrin, permethrin,
cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropathrin,
tralomethrin, cycloprothrin, flucythrinate, fluvalinate,
acrinathrin, tefluthrin, bifenthrin, empenthrin, beta-cyfluthrin,
zeta-cypermethrin, and fenvalerate, and various isomers thereof and
pyrethrum extracts; organophosphate insecticides such as DDVP,
cyanophos, fenthion, fenitrothion, tetrachlorvinphos,
dimethylvinphos, propaphos, methylparathion, temephos, phoxim,
acephate, isofenphos, salithion, DEP, EPN, ethion, mecarbam,
pyridafenthion, diazinon, pirimiphos-methyl, etrimfos, isoxathion,
quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet,
methidathion, oxydeprofos, vamidothion, malathion, phenthoate,
dimethoate, formothion, thiometon, ethylthiometon, phorate,
terbufos, profenofos, prothiofos, sulprofos, pyraclofos,
monocrotophos, naled, fosthiazate, and cadusafos; carbamate
insecticides such as NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC,
ethiofencarb, bendiocarb, pirimicarb, carbosulfan, benfuracarb,
methomyl, oxamyl, and aldicarb; arylpropylether insecticides such
as etofenprox and halfenprox; silylether insecticides such as
silafluofen; insecticidal natural products such as
nicotine-sulfate, polynactin complex, abamectin, milbemectin, and
BT agents; insecticides such as, cartap, thiocyclam, bensultap,
diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron,
flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid,
nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil,
buprofezin, fenoxycarb, pyriproxyfen, methoprene, hydroprene,
kinoprene, diafenthiuron, triazamate, tebufenozide, and endosulfan;
acaricides such as dicofol, chlorobenzilate, bromopropylate,
tetradifon, CPCBS, BPPS, chinomethionate, amitraz, benzoximate,
hexythiazox, fenbutatin oxide, cyhexatin, dienochlor, clofentezine,
pyridaben, fenpyroximate, fenazaquin, and tebufenpyrad; and other
insecticides such as novaluron, noviflumuron, emamectin benzoate,
clothianidin, thiacloprid, thiamethoxam, flupyrazofos, acequinocyl,
bifenazate, chromafenozide, etoxazole, fluacrypyrim, flufenzine,
halofenozide, indoxacarb, methoxyfenozide, spirodiclofen,
tolfenpyrad, gamma-cyhalothrin, ethiprole, amidoflumet,
bistrifluron, flonicamid, flubrocythrinate, flufenerim, pyridalyl,
pyrimidifen, spinosad, and spiromesifen.
[0156] Examples of fungicides which can be combined with the
compounds represented by formula (1) of the present invention
include azole fungicides such as triadimefon, hexaconazole,
propiconazole, ipconazole, prochloraz, and triflumizole; pyrimidine
fungicides such as pyrifenox and fenarimol; anilinopyrimidine
fungicides such as mepanipyrim and cyprodinil; acylalanine
fungicides such as metalaxyl, oxadixyl, and benalaxyl;
benzimidazole fungicides such as thiophanate-methyl and benomyl;
dithiocarbamate fungicids such as mancozeb, propineb, zineb, and
metiram; organochlorine fungicides such as
tetrachloroisophthalonitrile; carboxamide fungicides such as
carpropamid and ethaboxam; morpholine fungicides such as
dimethomorph; strobilurin fungicides such as azoxystrobin,
kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin,
trifloxystrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin;
dicarboxyimide fungicides such as iprodione and procymidone;
soil-applied fungicides such as flusulfamide, dazomet, methyl
isothiocyanate, and chloropicrin; copper fungicides such as basic
copper chloride, basic copper sulfate, copper nonylphenol
sulfonate, oxine-copper, and DBEDC; inorganic fungicides such as
sulfur and zinc sulfate; organophosphate fungicides such as
edifenphos, tolclofos-methyl, and fosetyl-aluminum; melanin
biosynthesis inhibitors such as phthalide, tricyclazole,
pyroquilon, and diclocymet; antibiotics such as kasugamycin,
validamycin, and polyoxins; fungicidal natural products such as
repe seed oil; and other fungicides such as
benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid,
quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid,
proquinazid, silthiofam, oxypoconazole, famoxadone, cyazofamid,
fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole,
chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet,
dichlofluanid,
[0157]
(RS)--N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluorom-
ethyl-1H-pyrazole-4-carboxamide(penthiopyrad; ISO proposed),
oxycarboxin, mepronil, flutolanil, triforine, oxolinic acid,
probenazole, acibenzolar-5-methyl, isoprothiolane, ferimzone,
diclomezine, pencycuron, fluoroimide, chinomethionate,
iminoctadine-triacetate, and iminoctadine-albesilate.
[0158] When the compounds represented by formula (1) of the present
invention are combined with at lease one type of other insecticide
and/or fungicide, mixed compositions of the compounds represented
by formula (1) and other insecticides and/or fungicides may be
used, or the compounds represented by formula (1) may be mixed with
other insecticides and/or fungicides during agricultural
treatment.
[0159] Besides the above-described insecticides and fungicides, the
compounds represented by formula (1) may be mixed with a herbicide,
a fertilizer, an ameliorant, a plant protective such as a plant
growth regulator, or resources to form multipurpose compositions
having superior efficiency or compositions from which an additive
effect or a synergistic effect can be expected.
[0160] Although representative examples of the present invention
will be described below, the present invention is not limited to
these examples.
EXAMPLE 1
(1-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-nitrobenzamide
[0161] To a solution prepared by adding 20.0 g of
2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine
to 100 ml of tetrahydrofuran and then stirring the resultant
mixture at room temperature was dropwise added a solution of 13.0 g
of 3-nitrobenzoyl chloride in 20 ml of tetrahydrofuran. After the
resultant mixture was stirred at room temperature for 10 hours,
ethyl acetate and water were added to the reaction solution. Then,
a separating operation was performed, and an organic layer was
separated and then dried with anhydrous magnesium sulfate. The
solution was filtered, and then the filtrate was collected, and the
solvent of the filtrate was distilled off under reduced pressure.
The residue was washed with a n-hexane-diisopropyl ether solvent
mixture to obtain 26.0 g (yield 85%) of the title compound as a
white solid.
[0162] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.33 (6H, s), 7.37
(2H, s), 7.68 (1H, s), 7.72 (1H, t, J=8.1 Hz), 8.28 (1H, d, J=8.1
Hz), 8.44 (1H, dd, J=1.2 Hz, 8.1 Hz), 8.75 (1H, t, J=1.2 Hz)
(1-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-aminobenzamide
[0163] To a solution prepared by adding 0.90 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and
1.56 g of tin chloride anhydride to 25 ml of ethanol and stirring
the resultant mixture at room temperature was added 2 ml of conc.
hydrochloric acid. The resultant mixture was then stirred under
heating at 60.degree. C. for 1 hour. After the temperature was
returned to room temperature, the reaction solution was poured into
water and then neutralized with potassium carbonate. Then, ethyl
acetate was added to the reaction solution, and insoluble materials
were filtered off. Then, an organic layer was separated and then
dried with anhydrous magnesium sulfate. The solution was filtered,
and then the filtrate was collected, and the solvent of the
filtrate was distilled off under reduced pressure. The residue was
washed with hexane to obtain 0.44 g (yield 53%) of the title
compound as a white solid.
[0164] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.34 (6H, s), 3.87
(2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)
(1-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-(2-chloroethoxycarbonylamino)benzamide (Compound No. 130)
[0165] To a solution prepared by adding 0.20 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and
0.08 g of pyridine to 5 ml of tetrahydrofuran and stirring the
resultant mixture at room temperature was dropwise added a solution
of 0.07 g of 2-chloroethyl chloroformate in 1 ml of
tetrahydrofuran. After the resultant mixture was stirred for 2
hours, ethyl acetate and water were added to the reaction solution.
Then, a separating operation was performed, and an organic layer
was separated and then dried with anhydrous magnesium sulfate. The
solution was filtered, and then the filtrate was collected, and the
solvent of the filtrate was distilled off under reduced pressure.
The residue was purified by silica gel column chromatography
(eluent; hexane:ethyl acetate=4:1) to obtain 0.23 g (yield 91%) of
the title compound as a white solid.
[0166] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.35 (6H, s),
3.74-3.77 (2H, m), 4.44-4.47 (2H, m), 6.87 (1H, broad), 7.36 (2H,
s), 7.43-7.52 (2H, m), 7.59-7.64 (2H, m), 8.02 (1H, s)
[0167] The compounds shown in Table 6 can be produced as production
intermediates useful for producing the compounds represented by
formula (1) of the present invention according to the processes
described in Examples 1-1 and 1-2.
EXAMPLE 2
Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-(ethylthiocarbonylamino)benzamide (Compound No. 1962)
[0168] To a solution prepared by adding 0.25 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide
produced in (1-2) of Example 1 and 0.06 g of pyridine to 5 ml of
tetrahydrofuran and then stirring the resultant mixture at room
temperature was dropwise added a solution of 0.08 g of ethyl
chlorothioformate in 1 ml of tetrahydrofuran. After the resultant
mixture was stirred for 2 hours, ethyl acetate and water were added
to the reaction solution. Then, a separating operation was
performed, and an organic layer was separated and then dried with
anhydrous magnesium sulfate. The solution was filtered, and then
the filtrate was collected, and the solvent of the filtrate was
distilled off under reduced pressure. The residue was washed with
hexane to obtain 0.27 g (yield 89%) of the title compound as a
white solid.
[0169] .sup.1H-NMR (CDCl.sub.3+DMSO-d.sub.6, ppm) .delta. 1.34 (3H,
t, J=7.3 Hz), 2.34 (6H, s), 2.96 (2H, q, J=7.3 Hz), 7.33 (2H, s),
7.41 (1H, t, J=7.8 Hz), 7.67 (1H, d, J=7.8 Hz), 7.83-7.85 (1H, m),
8.11 (1H, d, J=2.0 Hz), 8.79 (1H, s), 9.58 (1H, s)
EXAMPLE 3
Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-[(4-cyanobenzyl)oxycarbonylamino]benzamide (Compound No. 85)
[0170] To a solution prepared by adding 0.30 g 3-isocyanatobenzoyl
chloride to 10 ml of ether and then stirring the resultant mixture
at 2.degree. C. was dropwise added, over 5 minutes at a temperature
kept at 2.degree. C., a solution of 0.23 g of 4-cyanobenzyl alcohol
and 0.32 g of tri-n-butylamine in 5 ml of ether. After the
resultant mixture was stirred at 2.degree. C. for 2 hours, the
temperature was returned to room temperature, and then a solution
of 0.49 g of 2,6-dimethyl-4-heptafluoroisopropylaniline in 5 ml of
ether was dropwise added to the mixture, followed by stirring at
room temperature for 3 hours. Then, ethyl acetate was added to the
reaction solution, and the reaction solution was washed with water
twice. Then, an organic layer was dried with anhydrous magnesium
sulfate. The solution was filtered, and then the filtrate was
collected, and the solvent of the filtrate was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=2:1 to 1:1) to obtain
0.50 g (yield 40%) of the title compound as an oily material.
[0171] .sup.1H-NMR (CDCl, ppm) .delta. 2.34 (6H, s), 5.27 (2H, s),
6.97 (1H, broad-s), 7.35 (2H, s), 7.45-7.52 (4H, m), 7.61-7.69 (4H,
m), 8.01 (1H, s)
[0172] Similarly, N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzamide (Compound
No. 163) was produced by using
2-chloro-5-hydroxymethylpyridine.
[0173] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.34 (6H, s), 5.22
(2H, s), 6.89 (1H, broad-s), 7.35-7.49 (5H, m), 7.62 (2H, d, J=7.3
Hz), 7.72-7.77 (1H, m), 8.00 (1H, broad-s), 8.45 (1H, d, J=2.4
Hz)
[0174] N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-[(tetrahydrofuran-3-yl)methoxycarbonylamino]benzamide (Compound
No. 158) was produced by the same process as described above using
3-hydroxymethyltetrahydrofuran except that the solvent was changed
to tetrahydrofuran.
[0175] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 1.66-1.73 (1H, m),
2.05-2.13 (1H, m), 2.34 (6H, s), 2.60-2.70 (1H, m), 3.64-3.68 (1H,
m), 3.73-3.79 (1H, m), 3.85-3.92 (2H, m), 4.09-4.15 (2H, m), 6.87
(1H, broad-s), 7.35 (2H, s), 7.46 (2H, t, J=7.8 Hz), 7.61-7.66 (2H,
m), 8.01 (1H, broad-s)
EXAMPLE 4
(4-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-aminobenzthioamide
[0176] To 10 ml of toluene were added 0.35 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide
produced in Example (1-2) and 0.19 g of Lawesson's reagent. Then,
the resultant mixture was stirred under heating at a reflux
temperature for 6 hours. The reaction solution was concentrated
under reduced pressure, and the solvent was distilled off. The
residue was purified by silica gel column chromatography (eluent;
hexane ethyl acetate=3:1) to obtain 0.07 g (yield 20%) of the title
compound.
[0177] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.36 (6H, s), 3.87
(2H, broad-s), 6.84-6.87 (1H, m), 7.18-7.24 (2H, m), 7.33 (1H, s),
7.39 (2H, s), 8.56 (1H, broad-s)
(4-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-(2,2,2-trichloroethoxycarbonylamino)benzthioamide (Compound No.
1964)
[0178] To a solution prepared by adding 0.07 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide
and 0.03 g of pyridine to 5 ml of tetrahydrofuran and then stirring
the resultant mixture at room temperature was dropwise added a
solution of 0.05 g of 2,2,2-trichloroethyl chloroformate in 1 ml of
tetrahydrofuran. After the resultant mixture was stirred 2 hours,
ethyl acetate and water were added to the reaction solution, and a
separating operation was performed. Then, an organic layer was
separated and dried with anhydrous magnesium sulfate. The solution
was filtered, and then the filtrate was collected, and the solvent
of the filtrate was distilled off under reduced pressure. The
residue was purified by silica gel column chromatography (eluent;
hexane:ethyl acetate=4:1) to obtain 0.09 g (yield 90%) of the title
compound as a white solid.
[0179] .sup.1H-NMR(CDCl.sub.3, ppm) .delta. 2.37 (6H, s), 4.85 (2H,
s), 7.07 (1H, broad), 7.39 (2H, s), 7.45 (1H, t, J=8.1 Hz),
7.61-7.68 (2H, m), 8.11 (1H, s), 8.69(1H, s)
EXAMPLE 5
(5-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-chloropyridine-2-carboxamide
[0180] First, to a solution prepared by adding 2.36 g of
6-chloropyridine-2-carboxylic acid and 5 droplets of
N,N-dimethylformamide to 30 ml of toluene was added 2.14 g of
thionyl chloride, and then the resultant mixture was stirred under
heating at 80.degree. C. for 2 hours. Then, the solvent was
distilled off under reduced pressure, and the residue was dissolved
in 10 ml of tetrahydrofuran. The resultant solution was added
dropwise, at room temperature, to a solution obtained by adding
3.83 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.28 g of
pyridine to 20 ml of tetrahydrofuran, followed by stirring for 5
hours. Then, ethyl acetate and water were added to the reaction
solution, and a separating operation was performed. Then, an
organic layer was separated and dried with anhydrous magnesium
sulfate. The solution was filtered, and then the filtrate was
collected, and the solvent of the filtrate was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 3.90 g
(yield 67%) of the title compound as a solid.
[0181] .sup.1H-NMR(CDCl.sub.3, ppm) .delta. 2.36 (6H, s), 7.36 (2H,
s), 7.56 (1H, dd, J=1.0 Hz, 8.1 Hz), 7.88 (1H, dd, J=7.6 Hz, 8.1
Hz), 8.23 (1H, dd, J=1.0 Hz, 7.6 Hz), 9.27 (1H, broad-s)
(5-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-aminopyridine-2-carboxamide
[0182] In a 200 ml autoclave were charged 3.08 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-chloropyridien-2-carboxamide, 30 ml of 28% ammonia water, 0.20 g
of copper sulfate, and 70 ml of methanol, and the resultant mixture
was stirred under heating at 150.degree. C. for 2 hours. After the
mixture was cooled to room temperature, ammonia was distilled off
at 60.degree. C. under atmospheric pressure, and methanol was
distilled off under reduced pressure. Then, ethyl acetate and water
were added to the reaction solution, and a separating operation was
performed. Then, an organic layer was separated and dried with
anhydrous sodium sulfate. The solution was filtered, and then the
filtrate was collected, and the solvent of the filtrate was
distilled off under reduced pressure. The residue was purified by
silica gel column chromatography (eluent; hexane:ethyl acetate=3:2
to 2:3) to obtain 2.90 g (yield 98%) of the title compound as a
oily material.
[0183] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.35 (6H, s), 4.57
(2H, broad-s), 6.69-6.74 (1H, m), 7.34 (2H, s), 7.62-7.66 (2H, m),
9.39 (1H, broad-s)
(5-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(2,2,2-trichloroethoxycarbonylamino)pyridine-2-carboxamide
(Compound No. 1968)
[0184] To a solution prepared by adding 0.15 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-aminopyridine-2-carboxamide and 0.06 g of pyridine to 5 ml of
tetrahydrofuran and stirring the resultant mixture at room
temperature was dropwise added a solution of 0.085 g of
2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran.
After the resultant mixture was stirred for 2 hours, ethyl acetate
and water were added to the reaction solution, and a separating
operation was performed. Then, an organic layer was separated and
dried with anhydrous magnesium sulfate. The solution was filtered,
and then the filtrate was collected, and the solvent of the
filtrate was distilled off under reduced pressure. The residue was
purified by silica gel column chromatography (eluent; hexane:ethyl
acetate=10:1) to obtain 0.13 g (yield 61%) of the title compound as
a white solid.
[0185] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.35 (6H, s), 4.89
(2H, s), 7.36 (2H, s), 7.63 (1H, broad-s), 7.97 (1H, dd, J=7.6 Hz,
8.3 Hz), 8.05 (1H, d, J=7.6 Hz), 8.21 (1H, d, J=8.3 Hz), 9.17 (1H,
broad-s)
(5-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(2,2,2-trichloroethoxycarbonylamino)pyridine-N-oxide-2-carboxamide
(Compound No. 2062)
[0186] To 10 ml of benzene was added 0.26 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(2,2,2-trichloroethoxycarbonylamino)pyridine-2-carboxamide
produced in Example 5-3, and then the resultant mixture was
stirred. Then, 0.08 g of m-chloroperbenzoic acid was added to the
mixture at room temperature. After the resultant mixture was
stirred at 70.degree. C. for 1 hour, 0.2 g of m-chloroperbenzoic
acid was further added to the mixture, followed by stirring at
70.degree. C. for 7 hours. Then, the mixture was diluted with ethyl
acetate, and an organic layer was washed with a saturated aqueous
solution of sodium hydrogen carbonate three times and dried with
anhydrous magnesium sulfate. Then, the solvent was distilled off
under reduced pressure. The residue was purified by silica gel
column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain
0.11 g (yield 41%) of the title compound as an amorphous
material.
[0187] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.37 (6H, s), 4.91
(2H, s), 7.36 (2H, s), 7.61 (1H, t, J=8.3 Hz), 8.23 (1H, dd, J=8.3
Hz, 1.9 Hz), 8.45 (1H, dd, J=8.3 Hz, 1.9 Hz), 9.81 (1H, broad-s),
12.70 (1H, broad-s)
(5-5) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(methylamino)pyridine-2-carboxamide
[0188] N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(methylamino)pyridine-2-carboxamide was produced by using
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-chloropyridine-2-carboxamide produced in Example 5-1 and a
methylamine aqueous solution as reaction materials according to the
process described in Example 5-2.
[0189] .sup.1H-NMR (DMSO-d.sub.6, ppm) .delta. 2.30 (6H, s), 2.92
(3H, s), 6.71 (1H, d, J=8.3 Hz), 6.85 (1H, d, J=4.9 Hz), 7.22 (1H,
d, J=7.0 Hz), 7.44 (2H, s), 7.55 (1H, dd, J=7.0 Hz, 8.3 Hz), 10.05
(1H, s)
(5-6) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide
(Compound No. 2168)
[0190] N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide
was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(methylamino)pyridine-2-carboxamide produced in Example 5-5 as a
starting material according to the process described in Example
5-3.
[0191] .sup.1H-NMR(DMSO-d.sub.6, ppm) .delta. 2.30 (6H, s), 3.61
(3H, s), 5.03 (2H, s), 7.47 (2H, s), 7.92 (1H, d, J=7.6 Hz), 7.98
(1H, d, J=7.6 Hz), 8.08 (1H, t, J=7.6 Hz), 10.18 (1H, s)
EXAMPLE 6
(6-1) Production of ethyl
3-(2,2,2-trichloroethoxycarbonylamino)benzoate
[0192] To a solution prepared by adding 1.0 g of ethyl
m-aminobenzoate and 0.72 g of pyridine to 10 ml of tetrahydrofuran
and stirring the resultant mixture at room temperature was dropwise
added a solution of 1.55 g of 2,2,2-trichloroethyl chloroformate in
5 ml of tetrahydrofuran. After the resultant mixture was stirred
for 2 hours, ethyl acetate and water were added to the reaction
solution, and a separating operation was performed. Then, an
organic layer was separated and dried with anhydrous magnesium
sulfate. The solution was filtered, and then the filtrate was
collected, and the solvent of the filtrate was distilled off under
reduced pressure. The residue was washed with hexane to obtain 1.89
g (yield 91%) of the title compound.
[0193] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 1.40 (3H, t, J=7.3
Hz), 4.38 (2H, q, J=7.3 Hz), 4.84 (2H, s), 6.96 (1H, broad-s), 7.43
(1H, t, J=7.8 Hz), 7.76-7.82 (2H, m), 7.99 (1H, t, J=2.0 Hz)
(6-2) Production of ethyl
3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoate
[0194] To a suspension of 0.14 g of 60% sodium hydride in 5 ml of
tetrahydrofuran was dropwise added a solution of 1.0 g of ethyl
3-(2,2,2-trichloroethoxycarbonylamino)benzoate in 5 ml of
tetrahydrofuran, and the resultant mixture was stirred at room
temperature. Then, a solution of 0.45 g of dimethyl sulfate in 5 ml
of tetrahydrofuran was dropwise added, and the resultant mixture
was stirred at room temperature for 3 hours. After water was added
to the mixture, the mixture was subjected to extraction with ethyl
acetate, and an organic layer was washed twice with water and dried
with anhydrous magnesium sulfate. Then, the solvent was distilled
off under reduced pressure. The residue was purified by silica gel
column chromatography (eluent; hexane ethyl acetate=4:1) to obtain
0.84 g (yield 79%) of the title compound as an oily material.
[0195] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 1.40 (3H, t, J=7.1
Hz), 3.41 (3H, s), 4.39 (2H, q, J=7.1 Hz), 4.77 (2H, s), 7.43-7.52
(2H, m), 7.93-8.01 (2H, m)
(6-3) Production of
3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoic acid
[0196] To 5 ml of ethanol were added 0.5 g of ethyl
3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoate and a
1N sodium hydroxide aqueous solution, and the resultant mixture was
stirred at room temperature for 1.5 hours. After the reaction
solution was controlled to pH 3 by dropwise adding 1N hydrochloric
acid, ethyl acetate was added to the reaction solution, and an
organic layer was separated. The organic layer was washed with
water twice and washed with a saturated saline solution once, and
then dried with anhydrous magnesium sulfate. The solvent was
distilled off under reduced pressure to obtain 0.45 g (yield 98%)
of the title compound as a solid.
[0197] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.43 (3H, s), 4.79
(2H, s), 7.41-7.60 (2H, m), 7.93-8.05 (2H, m)
(6-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-[N'-methyl-N'-(2,2,2-trichloroethoxycarbonyl)amino]benzamide
(Compound No. 1958)
[0198] A solution of 0.30 g of
3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoic acid and
0.07 g of N-methylmorpholine in 5 ml of tetrahydrofuran was stirred
under cooling at -15.degree. C. A solution of 0.09 g of isopropyl
chloroformate in 5 ml of tetrahydrofuran was dropwise added to the
solution, and then a solution of 0.20 g of
2,6-dimethyl-4-heptafluoroisopropylaniline in 5 ml of
tetrahydrofuran was dropwise added to the resultant mixture. Then,
the resultant mixture was stirred at -15.degree. C. for 1 hour and
at room temperature for 24 hours. After the temperature was
returned to room temperature, ethyl acetate and water were added to
the reaction solution, and a separating operation was performed.
Then, an organic layer was washed with water twice and dried with
anhydrous magnesium sulfate. The solvent was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=4:1 to 2:1) to obtain
0.05 g (yield 5%) of the title compound as an oily material.
[0199] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.34 (6H, s), 3.45
(3H, s), 4.80 (2H, s), 7.36 (2H, s), 7.50-7.56 (3H, m), 7.78 (1H,
d, J=6.1 Hz), 7.90(1H, s)
EXAMPLE 7
(7-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-iodo-5-aminobenzamide
[0200] To a solution prepared by adding 0.70 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide
produced in Example 1-2 to 8 ml of N,N-dimethylformamide and then
stirring the resultant mixture in an iced water bath was dropwise
added a solution of 0.39 g of N-iodosuccinimide in 2 ml of
N,N-dimethylformamide. After the dropwise addition, the temperature
was returned to room temperature, and then mixture was further
stirred for 3 hours. Then, ethyl acetate and water were added to
the reaction solution, and a separating operation was performed.
Then, an organic layer was separated and dried with anhydrous
magnesium sulfate. The solvent was distilled off under reduced
pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=3:2) to obtain 0.67 g
(yield 73%) of the title compound as a solid.
[0201] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.44 (6H, s), 3.86
(2H, broad-s), 6.52 (1H, dd, J=2.9 Hz, 8.5 Hz), 6.91 (1H, d, J=2.9
Hz), 7.12 (1H, s), 7.35 (2H, s), 7.62 (1H, d, J=8.5 Hz)
(7-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-iodo-5-(isopropyloxycarbonylamino)benzamide (Compound No.
1945)
[0202] To a solution obtained by adding 0.20 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-iodo-5-aminobenzamide and 0.06 g of pyridine to 5 ml of
tetrahydrofuran and then stirring the mixture at room temperature
was dropwise added a solution of 0.05 g of isopropyl chloroformate
in 1 ml of tetrahydrofuran. After reaction for 2 hours, ethyl
acetate and water were added to the reaction solution, and a
separating operation was performed. Then, an organic layer was
separated and dried with anhydrous magnesium sulfate. The solution
was filtered, and then the filtrate was collected, and the solvent
of the filtrate was distilled off under reduced pressure. The
residue was purified by silica gel column chromatography (eluent;
hexane:ethyl acetate=4:1) to obtain 0.22 g (yield 96%) of the title
compound as a solid.
[0203] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 1.31 (6H, d, J=6.3
Hz), 2.45 (6H, s), 5.03 (1H, septet, J=6.3 Hz), 6.66 (1H, s),
7.16-7.21 (2H, m), 7.36 (2H, s), 7.76 (1H, s), 7.82 (1H, dd, J=2.7
Hz, 8.8 Hz)
EXAMPLE 8
(8-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-chloro-3-nitrobenzamide
[0204] First, to a solution prepared by adding 2.50 g of
2-chloro-3-nitrobenzoic acid and 5 droplets of
N,N-dimethylformamide to 30 ml of toluene was added 1.62 g of
thionyl chloride, and the resultant mixture was stirred under
heating at 80.degree. C. for 2 hours. Then, the solvent was
distilled off under reduced pressure, and the residue was dissolved
in 10 ml of tetrahydrofuran. The resultant solution was dropwise
added to a solution of 3.24 g of
2,6-dimethyl-4-heptafluoroisopropylaniline and 1.77 g of pyridine
in 20 ml of tetrahydrofuran at room temperature, and the mixture
was stirred for 5 hours. Then, ethyl acetate and water were added
to the reaction solution, and a separating operation was performed.
Then, an organic layer was separated and dried with anhydrous
magnesium sulfate. The solution was filtered, and then the filtrate
was collected, and the solvent of the filtrate was distilled off
under reduced pressure. The residue was purified by silica gel
column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain
3.38 g (yield 64%) of the title compound as a solid.
[0205] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.42 (6H, s), 7.34
(1H, s), 7.37 (1H, s), 7.55 (1H, t, J=7.8 Hz), 7.80 (1H, dd, J=1.5
Hz, 7.8 Hz), 7.86 (1H, dd, J=1.5 Hz, 7.8 Hz), 9.58 (1H, s)
(8-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-fluoro-3-nitrobenzamide
[0206] To 25 ml of N,N-dimethylformamide dried with molecular sieve
were added 2.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-chloro-3-nitrobenzamide and 0.87 g of potassium fluoride
(spray-dried), and the resultant mixture was stirred under heating
at 150.degree. C. for 3 hours. After the temperature was returned
to room temperature, ethyl acetate and water were added to the
reaction solution, and a separating operation was performed. Then,
an organic layer was separated, washed with water twice, and dried
with anhydrous magnesium sulfate. The solution was filtered, and
then the filtrate was collected, and the solvent of the filtrate
was distilled off under reduced pressure. The residue was purified
by silica gel column chromatography (eluent; hexane ethyl
acetate=4:1) to obtain 1.02 g (yield 45%) of the title compound as
a solid.
[0207] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.37 (6H, s), 7.39
(2H, s), 7.48-7.53 (1H, m), 7.87 (1H, d, J=11.5 Hz), 8.23-8.28 (1H,
m), 8.42-8.46 (1H, m)
(8-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-fluoro-3-aminobenzamide
[0208] The title compound was produced by using
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-fluoro-3-nitrobenzamide produced in Example 8-2 as a starting
material according to the same process as in Example 1-2 (yield
72%).
[0209] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.37 (6H, s), 3.90
(2H, broad-s), 6.96-7.01 (1H, m), 7.10 (1H, t, J=7.8 Hz), 7.36 (2H,
s), 7.43-7.47 (1H, m), 7.86 (1H, d, J=13.2 Hz)
(8-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-fluoro-3-(isopropyloxycarbonylamino)benzamide (Compound No.
1389)
[0210] The title compound was produced by using
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-fluoro-3-aminobenzamide produced in Example 8-3 as a starting
material according to the same process as in Example 7-2 (yield
72%).
[0211] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 1.34 (6H, d, J=6.3
Hz), 2.36 (6H, s), 5.07 (1H, septet, J=6.3 Hz), 6.86 (1H, broad-s),
7.30 (1H, t, J=8.1 Hz), 7.37 (2H, s), 7.72-7.79 (2H, m), 8.32 (1H,
broad)
EXAMPLE 9
(9-1) Production of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoic
acid
[0212] To an aqueous solution (200 ml) of 8.22 g of m-aminobenzoic
acid and 4.8 g of sodium hydroxide was dropwise added 25.0 g of
2,2,2-trichloroethyl chloroformate at room temperature. During the
dropwise addition, the reaction solution was controlled to pH 10 or
more by appropriately adding a 1N sodium hydroxide aqueous
solution. After the reaction, the solution was controlled to pH 1
by adding 1N hydrochloric acid, and the precipitates were collected
by filtration. The resultant crude crystals were dried and then
washed with a ethyl acetate/n-hexane mixed solvent to obtain 16.2 g
(yield 87%) of the title compound as a solid.
[0213] .sup.1H-NMR (DMSO-d.sub.6, ppm) .delta. 4.85 (2H, s), 7.38
(1H, d, J=7.8 Hz), 7.75 (1H, d, J=7.8 Hz), 7.79-7.80 (1H, m), 8.14
(1H, s), 9.02 (1H, s)
(9-2) Production of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl
chloride
[0214] To a toluene solution (10 ml) of 1.0 g of
3-[(2,2,2-trichloroethoxy)carbonylamino]benzoic acid produced in
Example 9-1 was added 2 ml of thionyl chloride, and the resultant
mixture was stirred at 100.degree. C. The solvent was distilled off
under reduced pressure, and the residue was dissolved in toluene.
The solvent was again distilled off under reduced pressure to
obtain 1.0 g (yield 95%) of the title compound as a solid.
[0215] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.86 (2H, s), 7.00
(1H, broad-s), 7.51 (1H, t, J=7.8 Hz), 7.84 (1H, d, J=7.8 Hz), 7.88
(1H, d, J=7.8 Hz), 8.16 (1H, s)
[0216] (9-3) Production of
N-(2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
3-[(2,2,2-trichloroethoxy)carbonylamino]benzamide (Compound No.
257) First, to a solution prepared by adding 0.34 g of
2,6-dimethyl-4-(nonafluoro-2-butyl)aniline and 0.09 g of pyridine
to 5 ml of tetrahydrofuran and stirring the resultant mixture at
room temperature was added 0.33 g of
3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl chloride produced
in Example 9-2. After reaction for 5 hours, ethyl acetate and water
were added to the reaction solution, and a separating operation was
performed. Then, an organic layer was separated and dried with
anhydrous magnesium sulfate. The solution was filtered, and then
the filtrate was collected, and the solvent of the filtrate was
distilled off under reduced pressure. The residue was purified by
silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)
to obtain 0.45 g (yield 71%) of the title compound as a solid.
[0217] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.34 (6H, s), 4.85
(2H, s), 7.10 (1H, s), 7.34 (2H, s), 7.47-7.51 (2H, m), 7.63-7.67
(2H, m), 8.05 (1H, s)
[0218] The following compounds were produced according to the
processes described in Examples 9-1 and 9-2. [0219]
3-(ethoxycarbonylamino)benzoyl chloride [0220]
3-(isopropylpropyloxycarbonylamino)benzoyl chloride [0221]
3-[(cyclobutyloxy)carbonylamino]benzoyl chloride [0222]
3-[(cyclopentyloxy)carbonylamino]benzoyl chloride [0223]
3-[(3-cyanobenzyloxy)carbonylamino]benzoyl chloride [0224]
3-[(4-cyanobenzyloxy)carbonylamino]benzoyl chloride [0225]
3-[(2-cyanoethoxy)carbonylamino]benzoyl chloride [0226]
3-[(2-methylthioethoxy)carbonylamino]benzoyl chloride [0227]
3-[(2-ethylthioethoxy)carbonylamino]benzoyl chloride [0228]
3-[(2-ethylsulfinylethoxy)carbonylamino]benzoyl chloride [0229]
3-[(2-fluoroethoxy)carbonylamino]benzoyl chloride [0230]
3-[(2,2-difluoroethoxy)carbonylamino]benzoyl chloride [0231]
3-[(2,2,2-trifluoroethoxy)carbonylamino]benzoyl chloride [0232]
3-[(1,3-difluoro-2-propyloxy)carbonylamino]benzoyl chloride [0233]
3-[(1-chloro-3-fluoro-2-propyloxy)carbonylamino]benzoyl chloride
[0234] 3-[(3,3,3-trifluoro-n-propyloxy)carbonylamino]benzoyl
chloride [0235]
3-[(2,2,3,3,3-pentafluoro-n-propyloxy)carbonylamino]benzoyl
chloride [0236]
3-[(4,4,4-trifluoro-n-butyloxy)carbonylamino]benzoyl chloride
[0237] 3-[(2,2,3,3-tetrafluorocyclobutyloxy)carbonylamino]benzoyl
chloride [0238] 3-[(2-chloroethoxy)carbonylamino]benzoyl chloride
[0239] 3-[(2,2-dichloroethoxy)carbonylamino]benzoyl chloride [0240]
3-[(1,3-dichloro-2-propyloxy)carbonylamino]benzoyl chloride [0241]
3-[(3-chloro-n-propyloxy)carbonylamino]benzoyl chloride [0242]
3-[(2-bromoethoxy)carbonylamino]benzoyl chloride [0243]
3-[(3-bromo-n-propyloxy)carbonylamino]benzoyl chloride [0244]
3-[(2-iodoethoxy)carbonylamino]benzoyl chloride [0245]
3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzoyl chloride
EXAMPLE 10
[0245] (10-1) Production of
N-(2,4-bistrifluoromethylphenyl)3-isocyanatobenzamide
[0246] To a 1,4-dioxane solution (20 ml) of 0.57 g of phosgene
dimmer was added a 1,4-dioxane solution (5 ml) of 2.0 g of
N-(2,4-bistrifluoromethylphenyl) 3-aminobenzamide (produced by
using 2,4-bistrifluoromethylaniline as a starting material
according to the process described in Example 1-2), and the
resultant mixture was stirred at 60.degree. C. for 3 hours. Then,
the solvent was distilled off under reduced pressure, and the
residue was dissolved in 10 ml of 1,4-dioxane. Then, the solvent
was again distilled off under reduced pressure. The product was
washed with n-hexane and filtered off to obtain 1.54 g (yield 72%)
of the title compound.
[0247] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.33-7.36 (1H, m),
7.51 (1H, t, J=7.8 Hz), 7.62-7.65 (2H, m), 7.88-7.92 (2H, m), 8.31
(1H, broad-s), 8.70 (1H, d, J=8.8 Hz)
(10-2) Production of
N-(2,4-bistrifluoromethylphenyl)3-[(2,2,3,3,3-pentafluoro-n-propyloxy)car-
bonylamino]benzamide (Compound No. 250)
[0248] First, to an anhydrous tetrahydrofuran solution (15 ml) of
0.5 g of N-(2,4-bistrifluoromethylphenyl)3-isocyanatobenzamide
produced in Example 10-1 were added 0.40 g of
2,2,3,3,3-pentafluoro-n-propanol and 0.13 g of triethylamine, and
the resultant mixture was stirred at room temperature for 5 hours.
The mixture was diluted with ethyl acetate (20 ml), and an organic
layer was washed with a 1N sodium hydroxide aqueous solution and 1N
hydrochloric acid. The solvent was distilled off under reduced
pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.49 g
(yield 70%) of the title compound.
[0249] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.68 (2H, t, J=13.2
Hz), 7.08 (1H, broad-s), 7.50-7.59 (2H, m), 7.70 (1H, broad-s),
7.87-7.92 (2H, m), 8.00 (1H, s), 8.39 (1H, s), 8.71 (1H, d, J=8.8
Hz)
EXAMPLE 11
(11-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-(benzyloxycarbonyl)benzamide
[0250] A mixture of 3.24 g of benzyl alcohol and 2.85 g of pyridine
was dropwise added to a tetrahydrofuran solution (60 ml) of 6.09 g
of isophthaloyl chloride at room temperature. After the resultant
mixture was stirred for 2 hours, a tetrahydrofuran solution (10 ml)
of 2,6-dimethyl-4-heptafluoroisopropylaniline was added to the
mixture in an ice bath, followed by stirring at room temperature
for 2 hours. The reaction solution was diluted with ethyl acetate
(50 ml), and an organic layer was washed with 1N hydrochloric acid.
The solvent was distilled off under reduced pressure. The residue
was purified by silica gel column chromatography (eluent; hexane
ethyl acetate=9:1) to obtain 9.5 g (yield 60%) of the title
compound as an amorphous material.
[0251] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.33 (6H, s), 5.41
(2H, s), 7.34-7.48 (7H, m), 7.56 (1H, s), 7.61 (1H, t, J=7.8 Hz),
8.17 (1H, t, J=7.8 Hz), 8.28 (1H, d, J=7.8 Hz), 8.57 (1H, s)
(11-2) Production of
3-[(2,6-dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic
acid
[0252] Catalytic hydrogen reduction was performed at normal
pressure by using a methanol solution (20 ml) of 2.0 g of
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-(benzyloxycarbonyl)benzamide produced in Example 11-1 and 0.2 g
of 10% palladium-carbon (wet, 50% product) to produce 1.59 g (yield
96%) of the title compound as a solid.
[0253] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.36 (6H,s), 7.37
(2H,s), 7.59 (1H,s), 7.67 (1H, t, J=7.8 Hz), 8.23 (1H, d, J=7.8
Hz), 8.32 (1H, d, J=7.8 Hz), 8.62 (1H, s)
(11-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropylphenyl)
3-isocyanatobenzamide
[0254] First, to an acetone solution (25 ml) of 1.4 g of
-[(2,6-dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic
acid produced in Example 11-2 and 0.38 g of triethylamine was added
0.44 g of ethyl chloroformate in an iced water bath, and the
resultant mixture was stirred at room temperature for 1 hour. Then,
an aqueous solution (10 ml) of 0.32 g of sodium azide was added to
the mixture, followed by stirring at room temperature for 2 hours.
The reaction solution was poured into iced water (150 ml), and the
precipitates were extracted with ethyl acetate (50 ml) and then
dried with anhydrous magnesium sulfate. After anhydrous magnesium
sulfate was filtered off, toluene (50 ml) was added to the
filtrate, and the low-boiling-point solvent was distilled off by
heating to 110.degree. C. using a Dean and Stark tube. After the
end of gas generation was confirmed, the temperature was returned
to room temperature, and then the residual solvent was distilled
off under reduced pressure to obtain 1.23 g (yield 88%) of the
title compound as a solid.
[0255] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.35 (6H, s), 7.32
(1H, d, J=7.8 Hz), 7.37 (2H,s), 7.39 (1H,s), 7.49 (1H, t, J=7.8
Hz), 7.67 (1H,s), 7.72 (1H, d, J=7.8 Hz)
(11-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropylphenyl)
3-[(1-chloro-3-trifluoromethyl-2-propyl)oxycarbonylamino]benzamide
(Compound No. 120)
[0256] The title compound was produced by using
N-(2,6-dimethyl-4-heptafluoroisopropylphenyl) 3-isocyanatobenzamide
produced in Example 11-3 according to the process described in
Example 10-2.
[0257] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.35 (6H, s),
3.75-3.83 (2H, m), 4.46-4.80 (2H, m), 5.19-5.24 (1H,m), 6.97 (1H,
broad-s), 7.36 (2H, s), 7.36-7.48 (2H, m), 7.60-7.66 (2H, m), 8.03
(1H, s)
[0258] The following compounds were produced according to the
processes described in Examples 10 and 11. [0259]
N-2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 3-isocyanatobenzamide
[0260] N-2,6-dimethyl-4-[(heptafluoro-n-propyl)thio]phenyl
3-isocyanatobenzamide [0261]
N-2,6-dibromo-4-[(heptafluoro-n-propyl)thio]phenyl
3-isocyanatobenzamide [0262]
N-2,6-dichloro-4-[(heptafluoro-n-propyl)thio]phenyl
3-isocyanatobenzamide [0263]
N-2,6-dimethyl-4-[(heptafluoroisopropyl)thio]phenyl
3-isocyanatobenzamide [0264]
N-2,6-dibromo-4-[(heptafluoroisopropyl)thio]phenyl
3-isocyanatobenzamide [0265]
N-2,6-dichloro-4-[(heptafluoroisopropyl)thio]phenyl
3-isocyanatobenzamide [0266]
N-2,6-dimethyl-4-[(nonafluoro-2-butyl)thio]phenyl
3-isocyanatobenzamide [0267]
N-2,6-dibromo-4-[(nonafluoro-2-butyl)thio]phenyl
3-isocyanatobenzamide [0268]
N-2,6-dichloro-4-[(nonafluoro-2-butyl)thio]phenyl
3-isocyanatobenzamide [0269]
N-2,6-dimethyl-4-[(heptafluoro-n-propyl)sulfinyl]phenyl
3-isocyanatobenzamide [0270]
N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfinyl]phenyl
3-isocyanatobenzamide [0271]
N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfinyl]phenyl
3-isocyanatobenzamide [0272]
N-2,6-dimethyl-4-[(heptafluoro-n-propyl)sulfonyl]phenyl
3-isocyanatobenzamide [0273]
N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfonyl]phenyl
3-isocyanatobenzamide [0274]
N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfonyl]phenyl
3-isocyanatobenzamide
EXAMPLE 12
[0274] (12-1) Production of 4-(heptafluoro-n-propylthio)aniline
[0275] To an acetonitrile solution (20 ml) of 4-aminothiophenol
(1.25 g, 9.98 mmol) and triethylamine (1.11 g, 11.0 mmol) was added
1-iodoheptafluoro-n-propane (5.91 g, 19.9 mmol), and the resultant
mixture was stirred at room temperature for 3 hours. The mixture
was diluted with ether, and washed with a 1N sodium hydroxide
aqueous solution. Then, the product was purified by silica gel
column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain
1.85 g (yield 63%) of the title compound.
[0276] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.95 (2H, s), 6.66
(2H, d, J=8.8 Hz), 7.40 (2H, d, J=8.8 Hz)
(12-2) Production of
2,6-dibromo-4-(heptafluoro-n-propylthio)aniline
[0277] First, to a solution of 0.77 g of
4-(heptafluoro-n-propylthio)aniline produced in Example 12-1 in 15
ml of N,N-dimethylformamide was added 0.98 g of N-bromosuccinimide.
After the resultant mixture was stirred at 60.degree. C. for 2
hours, ether and water were added to the mixture. Then, an organic
layer was separated, washed with water twice and dried with
anhydrous magnesium sulfate. The solvent was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=9:1) to obtain 1.19 g
(yield 100%) of the title compound as a red oily material.
[0278] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.98 (2H, broad-s),
7.66 (2H, s)
(12-3) Production of
N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl
3-nitrobenzamide
[0279] To a solution prepared by adding 1.08 g of
2,6-dibromo-4-(heptafluoro-n-propylthio)aniline produced in Example
12-2 and 0.4 g of pyridine to 20 ml of tetrahydrofuran and stirring
the resultant mixture at room temperature was dropwise added a
solution of 0.55 g of 3-nitrobenzoyl chloride in 20 ml of
tetrahydrofuran. After the resultant mixture was stirred at room
temperature for 10 hours, ethyl acetate and water were added to the
reaction solution, and a separating operation was performed. Then,
an organic layer was separated and dried with anhydrous magnesium
sulfate. The solution was filtered, and then the filtrate was
collected, and the solvent of the filtrate was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.86 g
(yield 48%) of the title compound as a white solid.
[0280] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.73 (1H, s, J=7.8 Hz,
7.77 (1H, t, J=7.8 Hz), 7.96 (2H, s), 8.31 (1H, s), 8.47-8.50 (1H,
m), 8.79 (1H, t, J=2.0 Hz)
(12-4) Production of
N-{12,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl
3-aminobenzamide
[0281] To a solution prepared by adding 0.97 g of
N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide
produced in Example 12-3 and 0.95 g of tin(II) chloride (anhydrous)
to 20 ml of ethanol and stirring the resultant mixture at room
temperature was added 2 ml of conc. hydrochloric acid, and the
resultant mixture was stirred under heating at 60.degree. C. for 1
hour. After the temperature was returned to room temperature, the
reaction solution was poured into water, and the solution was
neutralized with potassium carbonate. Then, ethyl acetate was added
to the solution, and insoluble materials were filtered off. Then,
an organic layer was separated and dried with anhydrous magnesium
sulfate. The solution was filtered, and then the filtrate was
collected, and the solvent of the filtrate was distilled off under
reduced pressure. The residue was washed with hexane to obtain 0.75
g (yield 81%) of the title compound as a white solid.
[0282] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 3.89 (2H, broad-s),
6.90 (1H, dt, J=2.5 Hz, 6.4 Hz), 7.28-7.30 (3H, m), 7.60 (1H, s),
7.93 (2H, s)
(12-5) Production of
N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl
3-(2,2,2-trichloroethoxycarbonylamino)benzamide (Compound No.
612)
[0283] To a solution prepared by adding 0.10 g of
N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-aminobenzamide
and 0.02 g of pyridine to 5 ml of tetrahydrofuran and stirring the
resultant mixture at room temperature was dropwise added a solution
of 0.04 g of 2,2,2-trichloroethyl chloroformate in 1 ml of
tetrahydrofuran. After reaction for 2 hours, ethyl acetate and
water were added to the reaction solution, and a separating
operation was performed. Then, an organic layer was separated and
dried with anhydrous magnesium sulfate. The solution was filtered,
and then the filtrate was collected, and the solvent of the
filtrate was distilled off under reduced pressure. The residue was
purified by silica gel column chromatography (eluent; hexane:ethyl
acetate=4:1) to obtain 0.11 g (yield 84%) of the title compound as
a solid.
[0284] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.86 (2H, s), 7.45
(1H, t, J=7.8 Hz), 7.72 (1H, d, J=7.8 Hz), 7.93 (2H, s), 7.94 (1H,
broad-s), 8.13 (1H, s), 9.02 (1H, s), 9.17 (1H, s)
(12-6) Production of
N-{2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)}phenyl
3-nitrobenzamide and
N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)}phenyl
3-nitrobenzamide
[0285] A solution prepared by adding 0.5 g of
N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide
to 15 ml of chloroform was stirred at room temperature, and 0.5 g
of m-chloroperbenzoic acid was added to the mixture. After the
resultant mixture was stirred at room temperature for 1 week, an
aqueous solution of sodium hydrogen sulfite was added to the
mixture, followed by stirring. Then, an organic layer was separated
and washed with a 1N sodium hydroxide aqueous solution and
saturated saline water. Then, the solvent was distilled off under
reduced pressure. The residue was purified by silica gel column
chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.21 g
of N-({2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)}phenyl
3-nitrobenzamide and 0.12 g of
N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)}phenyl
3-nitrobenzamide as solids.
[0286] (sulfinyl compound) .sup.1H-NMR (CDCl.sub.3, ppm) .delta.
7.76-7.82 (2H, m), 8.06 (1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m),
8.49-8.53 (1H, m), 8.81 (1H, s)
(12-7) Production of
2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline
[0287] To 20 ml of DMF were added 3.0 g (1.3 mmol) of
2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmol) of
potassium carbonate, 0.75 g (0.65 mmol) of
tetrakis(triphenylphosphine) palladium, and 0.17 g (1.3 mmol) of
trimethylboroxine, and the resultant mixture was stirred at
135.degree. C. for 6 hours. After the reaction solution was cooled
to room temperature, insoluble materials were filtered off with
cerite. The filtrate was concentrated under reduced pressure. The
residue was purified by silica gel column chromatography (eluent;
n-hexane:ethyl acetate=12:1 to 4:1) to obtain 1.17 g (yield 55%) of
the title compound as an oily material.
[0288] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.17 (6H,s), 3.86 (2H,
broad-s), 7.22 (2H, s)
[0289] The following aniline derivatives can be produced according
to the processes described in Examples 12-1, 12-2, 12-6, and 12-7.
[0290] 2-methyl-4-(pentafluoroethylthio)aniline [0291]
2-methyl-4-(heptafluoro-n-propylthio) aniline
[0292] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.16 (3H, s), 3.90
(2H, broad-s), 6.65 (1H, d, J=8.3 Hz), 7.28-7.31 (2H, m) [0293]
2-bromo-4-(heptafluoro-n-propylthio)aniline
[0294] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.44 (2H, broad-s),
6.75 (1H, d, J=8.8 Hz), 7.36 (1H, dd, J=2.0 Hz, 8.8 Hz), 7.69 (1H,
d, J=2.0 Hz) [0295] 2-methyl-4-(heptafluoroisopropylthio)aniline
[0296] 2-methyl-4-(nonafluoro-n-butylthio)aniline [0297]
2-methyl-4-(pentafluoroethylsulfinyl)aniline [0298]
2-methyl-4-(heptafluoro-n-propylsulfinyl)aniline [0299]
2-methyl-4-(heptafluoroisopropylsulfinyl) aniline [0300]
2-methyl-4-(nonafluoro-n-butylsulfinyl)aniline [0301]
2-methyl-4-(pentafluoroethylsulfonyl)aniline [0302]
2-methyl-4-(heptafluoro-n-propylsulfonyl)aniline [0303]
2-methyl-4-(heptafluoroisopropylsulfonyl) aniline [0304]
2-methyl-4-(nonafluoro-n-butylsulfonyl)aniline [0305]
2,6-dichloro-4-(pentafluoroethylthio)aniline [0306]
2,6-dibromo-4-(pentafluoroethylthio)aniline [0307]
N-{2,6-dibromo-4-(pentafluoroethylthio)}phenyl 3-nitrobenzamide
[0308] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.73 (1H,s), 7.77 (1H,
t, J=7.8 Hz), 7.96 (2H, s), 8.32 (1H, d, J=7.8 Hz), 8.47-8.50 (1H,
m), 8.80 (1H, t, J=2.0 Hz) [0309]
2,6-dimethyl-4-(pentafluoroethylthio)aniline [0310]
2,6-dichloro-4-(heptafluoro-n-propylthio)aniline
[0311] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.82 (2H, broad-s),
7.48 (2H, s) [0312]
N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl
3-nitrobenzamide
[0313] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.70 (1H, s), 7.76
(2H, s), 7.77 (1H, t, J=7.8 Hz), 8.31 (1H, d, J=7.8 Hz), 8.48 (1H,
d, J=7.8 Hz), 8.78 (1H, t, J=2.0 Hz) [0314]
2,6-dibromo-4-(heptafluoro-n-propylthio)aniline
[0315] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 4.93 (2H, broad-s),
7.66 (2H, s) [0316]
2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline
[0317] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.17 (6H, s), 3.86
(2H, broad-s), 7.22 (2H, s) [0318]
N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl
2-chloro-3-nitrobenzamide
[0319] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.39 (6H, s), 7.30
(1H, s), 7.46 (2H, s), 7.57 (1H, t, J=7.8 Hz), 7.90 (1H, d, J=7.8
Hz), 7.91 (1H, d, J=7.8 Hz) [0320]
2-bromo-4-(heptafluoro-n-propyl)thio-6-methylaniline
[0321] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.22 (3H, s), 4.40
(2H, broad-s), 7.27 (1H, s), 7.60 (1H, d, J=2.0 Hz) [0322]
2,6-dichloro-4-(heptafluoroisopropylthio)aniline
[0323] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 6.40 (2H, s), 7.52
(2H, s) [0324] 2,6-dibromo-4-(heptafluoroisopropylthio)aniline
[0325] N-{2,6-dichloro-4-(heptafluoroisopropylthio)}phenyl
3-nitrobenzamide
[0326] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.73 (1H, s), 7.76
(1H, t, J=7.8 Hz), 7.95 (2H, s), 8.31 (1H, d, J=7.8 Hz), 8.48 (1H,
d, J=7.8 Hz), 8.79 (1H, t, J=1.5 Hz) [0327]
2,6-dimethyl-4-(heptafluoroisopropylthio)aniline [0328]
2,6-dichloro-4-(nonafluoro-n-butylthio)aniline [0329]
2,6-dibromo-4-(nonafluoro-n-butylthio)aniline [0330]
N-{2,6-dichloro-4-(nonafluoro-n-butylthio)}phenyl
3-nitrobenzamide
[0331] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.76 (1H,s), 7.77 (1H,
t, J=8.3 Hz), 7.96 (2H, s), 8.32 (1H, d, J=8.3 Hz), 8.48 (1H, d,
J=8.3 Hz), 8.80 (1H, t, J=2.0 Hz) [0332]
2,6-dimethyl-4-(nonafluoro-n-butylthio)aniline [0333]
2,6-dichloro-4-(pentafluoroethylsulfinyl)aniline [0334]
2,6-dibromo-4-(pentafluoroethylsulfinyl)aniline [0335]
2,6-dimethyl-4-(pentafluoroethylsulfinyl)aniline [0336]
2,6-dichloro-4-(heptafluoro-n-propylsulfinyl)aniline [0337]
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)aniline [0338]
N-{2,6-dichloro-4-(heptafluoro-n-propylsulfinyl)}phenyl
3-nitrobenzamide
[0339] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.76-7.82 (2H, m),
8.06(1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m), 8.49-8.53 (1H, m),
8.81(1H, s) [0340]
2,6-dimethyl-4-(heptafluoro-n-propylsulfinyl)aniline [0341]
2,6-dichloro-4-(heptafluoroisopropylsulfinyl)aniline [0342]
2,6-dibromo-4-(heptafluoroisopropylsulfinyl)aniline [0343]
2,6-dimethyl-4-(heptafluoroisopropylsulfinyl)aniline [0344]
2,6-dichloro-4-(nonafluoro-n-butylsulfinyl)aniline [0345]
2,6-dibromo-4-(nonafluoro-n-butylsulfinyl)aniline [0346]
2,6-dimethyl-4-(nonafluoro-n-butylsulfinyl)aniline [0347]
2,6-dichloro-4-(pentafluoroethylsulfonyl)aniline [0348]
2,6-dibromo-4-(pentafluoroethylsulfonyl)aniline [0349]
2,6-dimethyl-4-(pentafluoroethylsulfonyl)aniline [0350]
2,6-dichloro-4-(heptafluoro-n-propylsulfonyl)aniline [0351]
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)aniline [0352]
2,6-dimethyl-4-(heptafluoro-n-propylsulfonyl)aniline [0353]
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)aniline [0354]
N-{2,6-dichloro-4-(heptafluoroisopropylsulfonyl)}phenyl
3-nitrobenzamide
[0355] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 7.79 (1H, t, J=7.8
Hz), 7.98 (1H, s), 8.07 (2H, s), 8.33 (1H, d, J=7.8 Hz), 8.51 (1H,
d, J=7.8 Hz), 8.81 (1H, t, J=2.0 Hz) [0356]
2,6-dibromo-4-(heptafluoroisopropylsulfonyl)aniline [0357]
2,6-dimethyl-4-(heptafluoroisopropylsulfonyl)aniline [0358]
2,6-dichloro-4-(nonafluoro-n-butylsulfonyl)aniline [0359]
2,6-dibromo-4-(nonafluoro-n-butylsulfonyl)aniline [0360]
2,6-dimethyl-4-(nonafluoro-n-butylsulfonyl)aniline
EXAMPLE 13
[0360] (13-1) Production of
2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline
[0361] A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of
hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid
monohydrate was stirred under heating at 100.degree. C. for 5
hours. After the temperature was returned to room temperature, the
mixture was diluted with ethyl acetate and washed with a 1N sodium
hydroxide aqueous solution. Then, the solvent was distilled off
under reduced pressure, and the precipitated crude crystals were
washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g
(yield 78%) of the title compound as a solid.
[0362] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.20 (6H, s), 3.26
(1H, broad-s), 3.76 (2H, broad-s), 7.25 (2H, s)
(13-2) Production of
N-[2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)]phenyl
3-(2,2,2-trichloroethoxycarbonylamino)benzamide (Compound No.
872)
[0363] The title compound was produced as an amorphous material by
using
2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline
produced in Example 13-1 as a starting material according to the
process described in Example 9-3 (yield 92%).
[0364] .sup.1H-NMR (CDCl.sub.3, ppm) .delta. 2.31 (6H, s), 3.99
(1H, s), 4.85 (2H, s), 7.15 (1H, broad-s), 7.45-7.51 (4H, m),
7.64-7.66 (2H, m), 8.01 (1H, s)
[0365] Formulation examples containing the compounds represented by
formula (1) of the present invention as active ingredients are
shown below, however the present invention is not limited to these
examples. In each of the formulation examples, "part(s)" represents
"part(s) by weight".
FORMULATION EXAMPLE 1
[0366] A mixture of 20 parts of a compound represented by formula
(1) of the present invention, 10 parts of Sorpol 355S (surfactant
produced by Toho Chemical Industry Co., Ltd.), and 70 parts of
xylene was uniformly stirred to produce an emulsion.
FORMULATION EXAMPLE 2
[0367] A mixture of 10 parts of a compound represented by formula
(1) of the present invention, 2 parts of sodium
alkylnaphthalenesulfonate, 1 part of sodium lignin-sulfonate, 5
parts of white carbon, and 82 parts of diatomite was uniformly
stirred to produce a wettable powder.
FORMULATION EXAMPLE 3
[0368] A mixture of 0.3 parts of a compound represented by formula
(1) of the present invention and 0.3 parts of white carbon was
uniformly stirred, and 99.2 parts of clay and 0.2 parts of Driless
A (produced by Sankyo Co., Ltd.) were added to the mixture. The
resultant mixture was uniformly ground to produce a dust.
FORMULATION EXAMPLE 4
[0369] A mixture of 2 parts of a compound represented by formula
(1) of the present invention, 2 parts of white carbon, 2 parts of
sodium lignin-sulfonate, and 94 parts of bentonite was uniformly
ground, and then water was added to the mixture. The resultant
mixture was kneaded, granulated and then dried to produce
granules.
FORMULATION EXAMPLE 5
[0370] A mixture of 20 parts of a compound represented by formula
(1) of the present invention and 5 parts of a 20% aqueous solution
of polyvinyl alcohol was sufficiently stirred, and then 75 parts of
a 0.8% aqueous solution of xanthane gum was added to the mixture.
Then, the resultant mixture was again stirred to produce a flowable
agent.
[0371] Test examples for making clear that the compounds
represented by formula (1) of the present invention have excellent
insecticidal activity are shown below, however the present
invention is not limited to these examples.
TEST EXAMPLE 1
Insecticidal Test for Common Cutworm (Spodoptera litura)
[0372] A cabbage leaf piece was immersed in a solution prepared by
diluting a test compound to a predetermined concentration for 30
seconds, and then dried in air. Then, the cabbage leaf piece was
placed in a polyethylene cup of 7 cm-size in which 2nd-instar
larvae of common cutworm were placed. The cup was allowed to stand
in a thermostatic chamber at 25.degree. C. Three days after, the
numbers of living and dead larvae were counted. The test was
carried out in two replications each containing five larvae.
[0373] As a result, at a concentration of 1000 ppm, a mortality of
70% or more was exhibited by Compounds Nos. 20, 59, 60, 62, 64, 66,
75, 78, 79, 81, 83, 84, 85, 90, 91, 92, 106, 108, 109, 111, 112,
116, 117, 118, 119, 120, 121, 123, 124, 125, 126, 127, 130, 131,
132, 134, 135, 136, 137, 138, 139, 140, 155, 156, 161, 163, 165,
174, 175, 176, 180, 181, 184, 186, 189, 190, 192, 196, 197, 198,
205, 206, 207, 208, 209, 210, 212, 213, 215, 216, 217, 218, 219,
220, 221, 224, 225, 228, 229, 230, 231, 232, 233, 234, 235, 236,
237, 241, 246, 247, 248, 250, 251, 252, 253, 254, 255, 256, 257,
258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518, 565, 605,
612, 659, 706, 770, 800, 817, 818, 819, 854, 855, 856, 857, 843,
844, 846, 847, 864, 867, 872, 873, 878, 890, 891, 892, 898, 899,
900, 902, 903, 905, 913, 915, 916, 919, 920, 922, 932, 933, 944,
948, 992, 1010, 1039, 1086, 1104, 1180, 1198, 1227, 1245, 1274,
1292, 1321, 1361, 1368, 1388, 1389, 1408, 1411, 1416, 1418, 1421,
1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1922, 1923, 1924,
1925, 1926, 1929, 1931, 1932, 1935, 1939, 1941, 1942, 1943, 1944,
1945, 1947, 1948, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1958,
1959, 1963, 1964, 1967, 1968, 1969, 2061, 2062, 2164, 2165, and
2168.
TEST EXAMPLE 2
Insecticidal Test for Diamondback Moth (Plutella xylostella)
[0374] A cabbage leaf pieces was immersed in a solution prepared by
diluting a test compound to a predetermined concentration for 30
seconds, and then dried in air. Then, the leaf piece was placed in
a polyethylene cup of 7 cm-size in which 2nd-instar larvae of
common cutworm were placed. The cup was allowed to stand in a
thermostatic chamber at 25.degree. C. Three days after, the numbers
of living and dead larvae were counted. The test was carried out in
two replications each containing five larvae.
[0375] As a result, at a concentration of 1000 ppm, a mortality of
70% or more was exhibited by Compounds Nos. 3, 5, 7, 8, 20, 59, 60,
62, 66, 75, 77, 78, 79, 80, 84, 85, 92, 94, 95, 96, 99, 101, 103,
104, 106, 108, 109, 110, 111, 112, 113, 116, 117, 118, 119, 120,
121, 123, 126, 127, 130, 131, 132, 134, 136, 137, 138, 139, 140,
141, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 168, 171,
174, 175, 176, 180, 181, 183, 184, 186, 190, 192, 196, 197, 198,
201, 203, 204, 205, 206, 207, 208, 209, 212, 213, 214, 215, 217,
218, 219, 220, 221, 223, 224, 228, 229, 230, 231, 232, 233, 234,
235, 236, 237, 238, 246, 247, 248, 249, 250, 252, 253, 254, 255,
256, 257, 258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518,
565, 605, 612, 659, 706, 800, 817, 818, 819, 820, 829, 858, 863,
865, 867, 868, 871, 872, 873, 878, 896, 897, 898, 899, 900, 902,
908, 913, 915, 919, 920, 922, 930, 932, 933, 936, 939, 941, 942,
943, 944, 945, 947, 948, 992, 1010, 1039, 1086, 1104, 1180, 1227,
1245, 1274, 1292, 1321, 1361, 1368, 1388, 1389, 1408, 1411, 1416,
1418, 1421, 1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1916,
1923, 1926, 1928, 1929, 1931, 1933, 1939, 1945, 1947, 1950, 1951,
1952, 1953, 1954, 1955, 1956, 1958, 1959, 1963, 1964, 1967, 1968,
1969, 2061, 2062, 2164, 2165, 2167, and 2168.
TEST EXAMPLE 3
Insecticidal Test for Small Brown Planthopper (Laodelphax
striatellus)
[0376] An acetone solution prepared by diluting a test compound to
a predetermined concentration was sprayed on rice seedlings, and
the rice seedlings were dried in air. Ten small brown planthoppers
and an original chemical were used for the test. The rice seedlings
were allowed to stand in a thermostatic chamber at 25.degree. C.
Six days after, the number of living insects was examined, and
three days after, the number of dead insects was examined. The test
was carried out one replication containing ten insects.
[0377] As a result, at a concentration of 1000 ppm, a mortality of
70% or more was exhibited by Compounds Nos. 108, 127, 184, 196,
197, 205, 209, 212, 215, 1321, 1361, 1368, 1408, 1411, 1416, 1435,
1455, 1458, 1463, 1958, 1959, and 1968.
* * * * *